2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole and its preparation method and application

Abstract

The present invention discloses a 2-(((1H-benzimidazole-1-yl)methyl)sulfinyl)benzothiazole, a preparation method thereof, and an application thereof. The present invention prepares 2-(((1H-benzimidazole-1-yl)methyl)sulfinyl)benzothiazole by a one-step oxidation method. The production process is simpler, more efficient, and easy to operate, providing a solid foundation for the large-scale production of 2-(((1H-benzimidazole-1-yl)methyl)sulfinyl)benzothiazole. The 2-(((1H-benzimidazole-1-yl)methyl)sulfinyl)benzothiazole of the present invention can prevent metal corrosion in an alkaline environment, and the pH value of the test solution does not decrease significantly. In addition, the preparation method of the present invention is simple, and a high-purity 2-(((1H-benzimidazole-1-yl)methyl)sulfinyl)benzothiazole product can be obtained without any post-processing. Therefore, it shows broad application prospects in the field of metal corrosion protection.

Description

Technical Field

[0001] The present invention belongs to the technical field of metal corrosion protection, and in particular relates to 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole, a preparation method and application thereof. Background Art

[0002] Metal corrosion is a phenomenon in which metals are destroyed by chemical or electrochemical effects of the environment. Metal corrosion affects all areas of marginal industrial production, causing huge economic losses and leading to an increase in the use of metal materials, which is not conducive to energy conservation, emission reduction and environmental protection.

[0003] Metal corrosion mainly includes two forms: electrochemical corrosion and seawater corrosion. Electrochemical corrosion is the damage caused by the electrochemical reaction between the metal surface and the ion-conducting medium. Its main characteristic is that its reaction process can be divided into two relatively independent and simultaneous processes: the cathodic reaction and the anodic reaction. Its main feature is the existence of a charged interface layer between the metal and the electrolyte. Seawater corrosion refers to the corrosion of equipment and facilities used in the marine environment. Seawater has the highest salt content and a complex composition, making it a corrosive electrolyte. The high concentration of chloride ions and other halide ions in seawater can prevent and destroy the passivation of metals, making the anodic process easier to proceed. Under the pH conditions of seawater, seawater corrosion is an oxygen depolarization process, and the cathodic process controls the speed of the corrosion reaction.

[0004] For a long time, people have been using a variety of technologies to protect metals. One of the most effective and economical methods is to apply an anti-corrosion coating to the metal surface to isolate the corrosive medium from the metal substrate. However, during its use, the coating will produce microcracks due to changes in factors such as the environment or mechanical properties. Due to exposure to the atmosphere, the microcracks will gradually spread and expand, thereby accelerating the peeling and delamination of the coating at the metal-coating interface, reducing the service life and anti-corrosion ability of the coating, and also affecting the use of the metal. Therefore, there is a need for a metal preservative that can prevent the corrosion of metal materials and solve the problems of metal anti-corrosion coatings in the existing technology that are prone to cracking, flaking, and poor anti-corrosion effect. Summary of the Invention

[0005] In order to improve the above technical problems, the present invention provides 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole and its preparation method and application. The compound of the present invention can prevent metal corrosion in an alkaline environment and the pH value of the test solution does not decrease significantly.

[0006] In order to achieve the above object, the present invention provides a compound with a structure shown in Formula I:

[0007]

[0008] The present invention also provides a method for preparing the compound of the structure shown in the above formula I, its stereoisomers or pharmaceutically acceptable salts and hydrates, comprising reacting 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole with meta-chloroperbenzoic acid (MCPBA) to obtain the compound of the structure shown in formula I.

[0009] According to an embodiment of the present invention, the molar ratio of 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole to m-chloroperbenzoic acid is 1:(0.5-2), exemplified by 1:0.5, 1:1, and 1:2.

[0010] According to an embodiment of the present invention, the method for preparing the compound of the structure represented by Formula I can be carried out in the presence of a solvent such as an organic solvent. For example, the organic solvent can be selected from dichloromethane.

[0011] According to an embodiment of the present invention, the preparation method includes dissolving 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole in a solvent and then mixing it with meta-chloroperbenzoic acid (MCPBA). Preferably, the mixing temperature is -10 to 10°C, exemplified by -10°C, 0°C, 5°C, and 10°C.

[0012] According to an embodiment of the present invention, the reaction temperature is room temperature; the reaction temperature is 1 to 48 hours, exemplified by 1 hour, 4 hours, 8 hours, 12 hours, 24 hours, 36 hours, and 48 hours. In the present invention, room temperature refers to a temperature of 25°C.

[0013] According to an embodiment of the present invention, the preparation method further includes a step of isolating a solid product from the reaction mixture after the reaction is completed. For example, the solid product is obtained by spin-drying the solvent. Further, the preparation method also includes a step of purifying the product. For example, the purification can be performed by column chromatography. Preferably, the eluent for column chromatography separation is petroleum ether / ethyl acetate = 1: (1 to 5) (v / v), exemplified by 1: 1, 1: 2, and 1: 5.

[0014] Preferably, the synthetic route of the compound of formula I is as follows:

[0015]

[0016] According to an embodiment of the present invention, the method for preparing the compound of the structure shown in Formula I comprises the following steps:

[0017] (1) Under nitrogen protection, 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole was dissolved in a solvent, and then m-chloroperbenzoic acid was added, and the reaction was allowed to proceed overnight;

[0018] (2) After the reaction is completed, the solvent is concentrated and removed;

[0019] (3) The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as eluent to obtain the desired product.

[0020] According to an embodiment of the present invention, the 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole is prepared by reacting 1-chloromethyl-1H-benzimidazole with 2-mercaptobenzothiazole.

[0021] In one embodiment of the present invention, the molar ratio of 1-chloromethyl-1H-benzimidazole to 2-mercaptobenzothiazole is 1:(1-5), exemplified by 1:1, 1:2, and 1:5.

[0022] In one embodiment of the present invention, a base is preferably added during the reaction of 1-chloromethyl-1H-benzimidazole and 2-mercaptobenzothiazole.

[0023] In one embodiment of the present invention, the molar ratio of the 1-chloromethyl-1H-benzimidazole to the base is 1:(1-5), exemplified by 1:1, 1:2.2, and 1:5.

[0024] In one embodiment of the present invention, the base is selected from one, two or more of N,N-diisopropylethylamine (DIPEA), potassium carbonate, sodium tert-butoxide, potassium tert-butoxide, potassium phosphate and sodium acetate.

[0025] In one embodiment of the present invention, NaI is preferably added to the reaction of 1-chloromethyl-1H-benzimidazole and 2-mercaptobenzothiazole.

[0026] In one embodiment of the present invention, the molar ratio of 1-chloromethyl-1H-benzimidazole to NaI is 1:(1-5), exemplified by 1:1, 1:2, and 1:5.

[0027] In one embodiment of the present invention, the preparation method of 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole can be carried out in the presence of a solvent, such as an organic solvent. For example, the organic solvent can be selected from 1,2-dichloroethane and tetrahydrofuran.

[0028] In one embodiment of the present invention, the reaction temperature is 40-100°C, exemplified by 40°C, 60°C, 80°C, and 100°C; the reaction time is 1-48h, exemplified by 1h, 2h, 4h, 6h, 8h, 12h, 16h, 24h, 36h, and 48h.

[0029] In one embodiment of the present invention, the preparation method further comprises a step of isolating a solid product from the reaction mixture after the reaction is completed. For example, the solid product is obtained by spin-drying the solvent. Furthermore, the preparation method further comprises a step of purifying the product. For example, the purification can be performed by column chromatography. Preferably, the eluent for column chromatography separation is petroleum ether / ethyl acetate = (1 to 5): 1 (v / v), exemplified by 1:1, 2:1, and 5:1.

[0030] In one embodiment of the present invention, the preparation method of 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole comprises the following steps:

[0031] (1) Under nitrogen protection, a nucleophilic reagent 2-mercaptobenzothiazole, 1-chloromethyl-1H-benzimidazole, sodium iodide, a base, and a solvent are stirred to react;

[0032] (2) After the reaction is completed, cool to room temperature and concentrate to remove the solvent;

[0033] (3) The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as the eluent to obtain -(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole.

[0034] According to an embodiment of the present invention, the 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole is prepared by reacting (1H-benzimidazol-1-yl)methanol with 2-mercaptobenzothiazole.

[0035] In one embodiment of the present invention, the molar ratio of (1H-benzimidazol-1-yl)methanol to 2-mercaptobenzothiazole is 1:(1-5), exemplified by 1:1, 1:2, and 1:5.

[0036] In one embodiment of the present invention, in the reaction of (1H-benzimidazol-1-yl)methanol and 2-mercaptobenzothiazole, triphenylphosphine (PPh3) and diisopropyl azodicarboxylate (DIAD) are preferably added.

[0037] In one embodiment of the present invention, the molar ratio of 1-chloromethyl-1H-benzimidazole to triphenylphosphine (PPh3) is 1:(1-5), exemplified by 1:1, 1:3, and 1:5.

[0038] In one embodiment of the present invention, the molar ratio of 1-chloromethyl-1H-benzimidazole to diisopropyl azodicarboxylate (DIAD) is 1:(1-5), exemplified by 1:1, 1:3, and 1:5.

[0039] In one embodiment of the present invention, the preparation method of 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole can be carried out in the presence of a solvent such as an organic solvent. For example, the organic solvent can be selected from tetrahydrofuran.

[0040] In one embodiment of the present invention, the preparation method comprises dissolving (1H-benzimidazol-1-yl)methanol, 2-mercaptobenzothiazole, and triphenylphosphine (PPh3) in a solvent, and then mixing with diisopropyl azodicarboxylate (DIAD). Preferably, the mixing temperature is -10 to 10°C, exemplified by -10°C, 0°C, 5°C, and 10°C.

[0041] In one embodiment of the present invention, the reaction temperature is room temperature; the reaction temperature of 1 to 48 hours is exemplified by 1 hour, 4 hours, 8 hours, 12 hours, 24 hours, 36 hours, and 48 hours. In the present invention, room temperature refers to a temperature of 25°C.

[0042] In one embodiment of the present invention, the preparation method further comprises a step of isolating a solid product from the reaction mixture after the reaction is completed. For example, the solid product is obtained by spin-drying the solvent. Furthermore, the preparation method further comprises a step of purifying the product. For example, the purification can be performed by column chromatography. Preferably, the eluent for column chromatography separation is petroleum ether / ethyl acetate = (1 to 5): 1 (v / v), exemplified by 1:1, 3:1, and 5:1.

[0043] In one embodiment of the present invention, the preparation method of 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole comprises the following steps:

[0044] (1) Under nitrogen protection, (1H-benzimidazol-1-yl)methanol, nucleophile 2-mercaptobenzothiazole, and triphenylphosphine (PPh3) were dissolved in tetrahydrofuran, diisopropyl azodicarboxylate (DIAD) was added at low temperature, and then the temperature was raised and stirred for reaction;

[0045] (2) After the reaction is completed, the solvent is removed;

[0046] (3) The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as eluent to obtain the desired product.

[0047] According to an embodiment of the present invention, the 1-chloromethyl-1H-benzimidazole is prepared by a nucleophilic substitution reaction between 1-hydroxymethyl-1H-benzimidazole and a chlorinating agent.

[0048] In one embodiment of the present invention, the molar ratio of 1-hydroxymethyl-1H-benzimidazole to the chlorinating agent is 1:(1-10), exemplified by 1:1, 1:6, and 1:10.

[0049] In one embodiment of the present invention, the chlorinating agent is selected from thionyl chloride, phosphorus trichloride or phosphorus oxychloride.

[0050] In one embodiment of the present invention, the preparation method of 1-chloromethyl-1H-benzimidazole can be carried out in the presence of a solvent such as an organic solvent. For example, the organic solvent can be selected from chloroform.

[0051] According to an embodiment of the present invention, the reaction temperature is room temperature; the reaction time is 1 to 48 hours, exemplified by 1 hour, 2 hours, 4 hours, 6 hours, 8 hours, 12 hours, 16 hours, 24 hours, 36 hours, and 48 hours.

[0052] According to an embodiment of the present invention, the preparation method further comprises the step of separating the solid product from the reaction mixture after the reaction is completed. For example, the solid product is obtained by spin-drying the solvent.

[0053] According to an embodiment of the present invention, the 1-hydroxymethyl-1H-benzimidazole is prepared by reacting benzimidazole with formaldehyde.

[0054] In one embodiment of the present invention, the molar ratio of benzimidazole to formaldehyde is 1:(0.5-2), exemplified by 1:0.5, 1:1, and 1:2.

[0055] In one embodiment of the present invention, the preparation method of 1-hydroxymethyl-1H-benzimidazole can be carried out in the presence of a solvent such as an organic solvent. For example, the organic solvent can be selected from tetrahydrofuran.

[0056] In one embodiment of the present invention, the reaction temperature is room temperature; the reaction time is 1 to 48 hours, exemplified by 1 hour, 2 hours, 4 hours, 6 hours, 8 hours, 12 hours, 16 hours, 24 hours, 36 hours, and 48 hours.

[0057] In one embodiment of the present invention, the preparation method further comprises a step of isolating a solid product from the reaction mixture after the reaction is completed. For example, the solid product is obtained by spin-drying the solvent. Furthermore, the preparation method further comprises a step of purifying the product. For example, the purification can be performed by recrystallization. Preferably, the solvent for the recrystallization can be ethanol and water.

[0058] In one embodiment of the present invention, the synthetic route of 1-chloromethyl-1H-benzimidazole is as follows:

[0059]

[0060] The present invention also provides the use of the compound represented by the structure of formula I in cleaning and anti-corrosion of metal product surfaces.

[0061] The present invention also provides a detergent containing the compound with the structure shown in the above formula I.

[0062] The present invention also provides a preservative containing the compound with the structure shown in the above formula I.

[0063] According to an embodiment of the present invention, the preservative further comprises an auxiliary agent. Preferably, the auxiliary agent is selected from a sustained-release agent and / or a surfactant.

[0064] In one embodiment of the present invention, the sustained release agent is selected from triethanolamine borate.

[0065] In one embodiment of the present invention, the surfactant is 2-amino-2-methyl-propanol.

[0066] According to an embodiment of the present invention, the preservative further contains tetramethylammonium hydroxide.

[0067] According to an embodiment of the present invention, in the preservative, the mass of the compound of the structure shown in Formula I is 0.01 to 20% of the mass of tetramethylammonium hydroxide, and exemplified by 0.01%, 0.04%, 0.1%, 0.5%, 1%, 2%, 5%, 10%, 15%, and 20%.

[0068] The present invention also provides an anti-corrosion coating, which contains the compound with the structure shown in the above formula I and / or is prepared from the compound with the structure shown in the above formula I.

[0069] Beneficial effects of the present invention:

[0070] The present invention discloses 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole, its preparation method, and application. The present invention prepares 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole by a one-step oxidation method, which not only reduces the complexity of the production process, but also makes the production process simpler, more efficient, and easier to operate. At the same time, by selecting low-cost raw materials, the present invention significantly reduces production costs while ensuring product quality. The preparation method of the present invention has the excellent characteristics of simplicity, high efficiency, and low cost, providing a solid foundation for the large-scale production of 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole. The 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole of the present invention can prevent metal corrosion in an alkaline environment, and the pH value of the test solution does not decrease significantly. BRIEF DESCRIPTION OF THE DRAWINGS

[0071] Figure 1 The 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole compound prepared in Example 1 1 H NMR spectrum.

[0072] Figure 2 The 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole compound prepared in Example 1 13 C NMR spectrum.

[0073] Figure 3 This is the HRMS spectrum of the 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole compound prepared in Example 1.

[0074] Figure 4 The 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole compound prepared in Example 1 1 H NMR spectrum.

[0075] Figure 5 The 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole compound prepared in Example 1 13 C NMR spectrum.

[0076] Figure 6 This is the HRMS spectrum of the 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole compound prepared in Example 1. DETAILED DESCRIPTION

[0077] The technical solutions of the present invention will be described in further detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanations of the present invention and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are encompassed within the scope of protection that the present invention is intended to protect.

[0078] Unless otherwise specified, the raw materials and reagents used in the following examples are commercially available or can be prepared by known methods.

[0079] Example 1

[0080] This embodiment provides a method for preparing 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole, and the reaction equation is:

[0081]

[0082] The preparation method of 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole comprises the following steps:

[0083] (1) Under nitrogen protection, 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole (1.5 g, 5.0 mmol) and dichloromethane (40.0 mL) were added to a 100.0 mL reaction bottle in sequence. Then, m-chloroperbenzoic acid (0.86 g, 5.0 mmol) was added at 0°C, and the reaction was stirred at room temperature overnight.

[0084] (2) After stirring, the components were concentrated on a rotary evaporator without any post-treatment;

[0085] (3) The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate in a volume ratio of 1:2 as the eluent to obtain a colorless oil (yield: 37%), namely 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole, with the structural formula:

[0086] The basic parameters of the 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole compound prepared in this example are as follows:

[0087] 1 H NMR (400MHz, CDCl3) δ8.11(d,J=8.2Hz,1H),7.90(s,1H),7.82(d,J=8.0Hz,1H),7.72(d,J=8.0Hz,1H) ,7.58(t,J=7.7Hz,1H),7.46(t,J=7.5Hz,1H),7.17(m,2H),7.02(t,J=7.7Hz,1H),5.77-5.54(m,2H)( Figure 1 );

[0088] 13 C NMR (101MHz, CDCl3) δ173.8,153.8,143.3,136.1,133.4,127.4,126.7,124.1,123.6,123.1,122.4,120.7,109.4,67.1( Figure 2 );

[0089] HRMS (ESI) m / z measured the C 15 H 11 Molecular weight of N3OS2 [M+H] + is 314.04163, and its theoretical molecular weight is 314.04115 ( Figure 3 ).

[0090] Among them, the preparation method of 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole has the following reaction equation:

[0091]

[0092] A method for preparing 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole comprises the following steps:

[0093] (1) Under nitrogen protection, 2-mercaptobenzothiazole (1.67 g, 10.0 mmol), 1-chloromethyl-1H-benzimidazole (2.2 g, 11.0 mmol), sodium iodide (1.5 g, 10.0 mmol), potassium carbonate (3.0 g, 22.0 mmol), and 1,2-dichloroethane (50.0 mL) were added to a 250.0 mL reaction flask in sequence and stirred at 60°C for 16 h.

[0094] (2) After stirring for 16 h, the mixture was cooled to room temperature and concentrated on a rotary evaporator at 40 °C without any post-treatment;

[0095] (3) The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate in a volume ratio of 2:1 as the eluent to obtain a white solid (yield: 60%), namely 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole, with the structural formula:

[0096] The basic parameters of the 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole compound prepared in this example are as follows:

[0097] 1 H NMR (400MHz, CDCl3) δ8.29(s,1H),7.98(d,J=8.1Hz,1H),7.79(m,1H),7.73(d,J=9.2Hz,1H),7.54-7.43(m,2H),7.37-7.28(m,3H),6.10(s,2H)( Figure 4 );

[0098] 13 C NMR (101MHz, CDCl3) δ163.1,152.6,144.1,143.1,135.6,133.0,126.5,125.0,123.5,122.9,122.0,121.3,120.8,110.0,45.8( Figure 5 );

[0099] HRMS (ESI) m / z measured the 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole C prepared in this example 15 H 11 Molecular weight of N3S2 [M+H] + The theoretical molecular weight is 298.0467. Figure 6 ).

[0100] The preparation method of 1-chloromethyl-1H-benzimidazole has the following reaction equation:

[0101]

[0102] The preparation method of 1-chloromethyl-1H-benzimidazole comprises the following steps:

[0103] (1) Benzimidazole (10.0 g, 84.65 mmol) and tetrahydrofuran (250.0 mL) were added sequentially to a 250.0 mL reaction flask, followed by dropwise addition of formaldehyde solution (37% concentration, 6.8 g, 84.65 mmol), and the mixture was stirred at room temperature for 12 h.

[0104] (2) After stirring for 12 h, the components were concentrated on a rotary evaporator without any post-treatment;

[0105] (3) The crude product was recrystallized from ethanol and water and filtered to obtain a white solid (yield 64%), namely 1-hydroxymethyl-1H-benzimidazole, with the structural formula:

[0106] (4) 1-Hydroxymethyl-1H-benzimidazole (1.5 g, 10.0 mmol) and chloroform (50.0 mL) were added sequentially to a 250.0 mL reaction flask, followed by dropwise addition of thionyl chloride (7.1 g, 60.0 mmol), and the mixture was stirred at room temperature for 6 h.

[0107] (5) After stirring for 6 h, the components were concentrated on a rotary evaporator without any post-treatment to directly obtain the desired white solid (yield 89%), namely 1-chloromethyl-1H-benzimidazole, with the structural formula:

[0108]

[0109] Test Example 1

[0110] Add 10.0g of DEV base (a 2.38% aqueous solution of tetramethylammonium hydroxide) to a 20.0mL Erlenmeyer flask. Add a magnet and start electromagnetic stirring to mix the solution evenly. Set the water bath temperature to 25-27°C. Then cut the aluminum sheet into 1cm*1cm small squares and place them in the Erlenmeyer flask. After soaking for 1 hour, remove the sheet with tweezers, rinse both sides with distilled water several times, wipe dry, and weigh. Then, place the sheet back in the solution and soak for another 2 hours (a total of 3 hours). After that, weigh the corroded weight and measure the pH of the solution at 18°C. The results are shown in Table 1 below.

[0111] Table 1

[0112]

[0113] Test Example 2

[0114] To a 20.0 mL Erlenmeyer flask, add 10.0 g of DEV base (a 2.38% aqueous solution of tetramethylammonium hydroxide), 0.2 g of additive 1 (triethanolamine borate sustained-release agent), and 0.01 g of additive 2 (2-amino-2-methyl-propanol surfactant). Add a magnetic stirrer and stir until the solution is evenly mixed. Set the water bath temperature to 25-27°C. Then, cut the aluminum sheet into 1 cm x 1 cm squares and place them in the Erlenmeyer flask. After soaking for 1 hour, remove the sheet with tweezers, rinse both sides several times with distilled water, wipe dry, and weigh. Then, place the sheet back in the solution and soak for another 2 hours (for a total of 3 hours). After that, weigh the corroded sheet. The pH of the solution was then measured at 18°C. The results are shown in Table 2 below.

[0115] Table 2

[0116]

[0117] Test Example 3

[0118] To a 20.0 mL Erlenmeyer flask, add 10.0 g of DEV base (a 2.38% aqueous solution of tetramethylammonium hydroxide), 0.2 g of additive 1 (triethanolamine borate sustained-release agent), 0.01 g of additive 2 (2-amino-2-methyl-propanol surfactant), and 0.03 g of the 2-(((1H-benzimidazol-1-yl)methyl)sulfinyl)benzothiazole complexing agent prepared in Example 1 (insoluble, dispersed in the system). A magnet was added, and electromagnetic stirring was activated to mix the solution evenly. The water bath temperature was set to 25-27°C. Subsequently, the aluminum sheet was cut into 1 cm*1 cm squares and placed in the Erlenmeyer flask. After soaking for 1 hour, the sheet was removed with tweezers, rinsed several times on both sides with distilled water, wiped dry, and weighed. The sheet was then placed back into the solution and soaked for another 2 hours (total 3 hours). The corroded sheet was then weighed and the pH of the solution was measured at 18°C. The results are shown in Table 3 below.

[0119] Table 3

[0120]

[0121] The above describes the embodiments of the present invention. However, the present invention is not limited to the above embodiments. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included in the scope of protection of the present invention.

Claims

1. A compound having a structure shown in formula I:

2. The method for preparing the compound of formula (I) according to claim 1, characterized in that: The preparation method comprises reacting 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole with m-chloroperbenzoic acid (MCPBA) to obtain a compound having a structure shown in formula I.

3. The preparation method according to claim 2, wherein The molar ratio of the 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole to m-chloroperbenzoic acid is 1:(0.5-2).

4. The preparation method according to claim 2, wherein The preparation method of the compound represented by the structure of formula I is carried out in the presence of a solvent.

5. The preparation method according to claim 4, wherein The preparation method comprises dissolving 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole in a solvent, and then mixing the solvent with m-chloroperbenzoic acid (MCPBA), wherein the mixing temperature is -10 to 10°C.

6. The preparation method according to claim 2, wherein The reaction temperature is room temperature; the reaction time is 1 to 48 hours.

7. The preparation method according to claim 2, wherein The preparation method further comprises the step of separating a solid product from the reaction mixture after the reaction is completed.

8. The preparation method according to any one of claims 2 to 7, wherein The preparation method further comprises the step of purifying the product, wherein the purification is performed by column chromatography separation; The eluent for column chromatography separation is petroleum ether / ethyl acetate=1:(1-5) (v / v).

9. The preparation method according to any one of claims 2 to 7, wherein: The steps include: (1) Under nitrogen protection, 2-(((1H-benzo[d]imidazol-1-yl)methyl)thio)benzo[d]thiazole was dissolved in a solvent, and then m-chloroperbenzoic acid was added, and the reaction was allowed to proceed overnight; (2) After the reaction is completed, the solvent is concentrated and removed; (3) The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as eluent to obtain the desired product.

10. Use of the compound of formula I according to claim 1 in cleaning and anti-corrosion of metal product surfaces.

11. A detergent, characterized in that It contains the compound with the structure shown in formula I according to claim 1.

12. A preservative, characterized in that It contains the compound with the structure shown in formula I according to claim 1.

13. The preservative according to claim 12, wherein The preservative further contains an auxiliary agent, and the auxiliary agent is selected from a sustained-release agent and / or a surfactant.

14. The preservative according to claim 13, wherein The sustained-release agent is selected from triethanolamine borate.

15. The preservative according to claim 13, wherein The surfactant is 2-amino-2-methyl-propanol.

16. The preservative according to any one of claims 12 to 15, characterized in that The preservative also contains tetramethylammonium hydroxide.

17. The preservative according to claim 16, wherein In the preservative, the mass of the compound with the structure shown in Formula I is 0.01 to 20% of the mass of tetramethylammonium hydroxide.

18. An anti-corrosion coating, characterized in that: The invention contains the compound with the structure shown in formula I according to claim 1 and / or is prepared from the compound with the structure shown in formula I according to claim 1.

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