Novel benzamide compound and preparation method thereof

Abstract

The invention relates to the field of chemical medicine preparation, in particular to a benzamide compound and a preparation method thereof. The benzamide compound provided by the invention is 4-chloro-2-(methyl carbamoyl) phenyl-3-bromine-1-(3-chloropyridine-2-yl)-1H-pyrazole-5-carboxylic ester, the molecular formula is C17H11BrCL2N4O3, the benzamide compound is a novel benzamide insecticide, and compared with the previous benzamide insecticide, the benzamide compound has the advantages of abundant raw material source, low cost, low cost and the like. The insecticidal composition has the advantages of wide insecticidal spectrum, good effect, long lasting period, low resistance and the like.

Description

Technical Field

[0001] The present invention relates to the field of chemical preparation, and in particular to a novel benzamide compound and a preparation method thereof. Background Art

[0002] The present application relates to a novel benzamide compound and a method for preparing the benzamide compound. The benzamide compound in the present application is 4-chloro-2-(methylcarbamoyl)phenyl-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, with a molecular formula of C 17 H 11 BrCL 2 N 4 O 3 It can be used as an active ingredient in insecticides to effectively and broadly control chewing pests on fruit trees, vegetables, field crops, specialty crops and lawns. It can also control Colorado beetles, leafhoppers, etc. At the same time, it has an inhibitory effect on whiteflies. Summary of the invention

[0003] The present invention provides a novel benzamide compound: 4-chloro-2-(methylcarbamoyl)phenyl-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, whose molecular formula is C 17 H 11 BrCL 2 N 4 O 3 , the structural formula is:

[0004]

[0005] Furthermore, the present invention also provides a method for preparing the above-mentioned 4-chloro-2-(methylcarbamoyl)phenyl-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, the preparation method comprising the following steps:

[0006] Compound 1, methylamine hydrochloride, N,N-dimethylformamide and sodium bicarbonate are mixed to obtain compound 2; the structural formula of compound 1 is The structural formula of the compound 2 is

[0007]

[0008] Compound 3, thionyl chloride and N,N-dimethylformamide are mixed to obtain compound 4; the structural formula of compound 3 is The structural formula of compound 4 is

[0009]

[0010] Compound 2, dichloromethane, pyridine and compound 4 are mixed to obtain the benzamide compound.

[0011] Optionally, the compound 1, methylamine hydrochloride, N,N-dimethylformamide and sodium bicarbonate are mixed to obtain compound 2, comprising:

[0012] Adding compound 1, methylamine hydrochloride and N,N-dimethylformamide into a container in sequence, mixing and stirring to obtain a second mixture;

[0013] Sodium bicarbonate is added to the second mixture, stirred for a first preset time, and filtered to obtain compound 2.

[0014] Optionally, the compound 2, dichloromethane, pyridine and compound 4 are mixed to obtain the benzamide compound, comprising:

[0015] Add compound 2, dichloromethane and pyridine into a container in sequence, mix and stir to obtain a third mixture;

[0016] Dissolving compound 4 in dichloromethane to obtain a fourth mixed solution;

[0017] The fourth mixed solution is slowly dripped into the third mixed solution, and after stirring for a second preset time, ice water is poured into the solution, and the solution is filtered after cooling to obtain the benzamide compound.

[0018] Optionally, the molar ratio of the compound 1, methylamine hydrochloride and N,N-dimethylformamide is 0.8-1.5:8-15:8-15.

[0019] Optionally, the molar ratio of the compound 3 to the thionyl chloride is 0.8-1.5:25-37.

[0020] Optionally, the molar ratio of compound 2, compound 4 and pyridine is 0.8-1.5:1.0-1.5:4-7.

[0021] In the present invention, 4-chloro-2-(methylcarbamoyl)phenyl-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate has the advantages of convenient raw material source, broad insecticide spectrum, good effect, long lasting effect, low resistance and the like.

[0022] Based on the following detailed description of specific embodiments of the present invention in conjunction with the accompanying drawings, those skilled in the art will become more aware of the above and other objects, advantages and features of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Hereinafter, some specific embodiments of the present invention will be described in detail in an exemplary and non-limiting manner with reference to the accompanying drawings. The same reference numerals in the accompanying drawings indicate the same or similar components or parts. It should be understood by those skilled in the art that these drawings are not necessarily drawn to scale. In the accompanying drawings:

[0024] Figure 1 is a process flow chart of benzamide compounds according to one embodiment of the present invention;

[0025] Figure 2 is a process flow chart of benzamide compounds according to another embodiment of the present invention;

[0026] Figure 3 is a partial process flow chart according to one embodiment of the present invention;

[0027] Figure 4 is a partial process flow chart according to one embodiment of the present invention. DETAILED DESCRIPTION

[0028] Refer to the following Figures 1 to 4 To describe a novel benzamide compound and a method for preparing a benzamide compound according to an embodiment of the present invention. In the description of this embodiment, it should be understood that the terms "first" and "second" are only used for descriptive purposes and cannot be understood as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, the features defined as "first" and "second" may explicitly or implicitly include at least one of the features, that is, include one or more of the features. In the description of the present invention, the meaning of "multiple" is at least two, such as two, three, etc., unless otherwise clearly and specifically defined. When a feature "includes or contains" one or some of the features it covers, unless otherwise specifically described, this indication does not exclude other features and may further include other features.

[0029] In the description of the present embodiment, the description with reference to the terms "one embodiment", "some embodiments", "illustrative embodiments", "examples", "specific examples", or "some examples" means that the specific features, structures, materials, or characteristics described in conjunction with the embodiment or example are included in at least one embodiment or example of the present invention. In this specification, the schematic representation of the above terms does not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials, or characteristics described may be combined in any one or more embodiments or examples in a suitable manner.

[0030] Figure 1 FIG. 1 is a process flow chart of a benzamide compound according to an embodiment of the present invention. Figure 1 As shown, combined with Figures 2 to 4The present invention provides a novel benzamide compound, which is 4-chloro-2-(methylcarbamoyl)phenyl-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, with a molecular formula of C 17 H 11 BrCL 2 N 4 O 3 .

[0031] In this embodiment, 4-chloro-2-(methylcarbamoyl)phenyl-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate has the advantages of abundant raw material sources, broad insecticide spectrum, good effect, long lasting effect, and low resistance.

[0032] In some embodiments of the present invention, a method for preparing the above-mentioned benzamide compound is also provided, and the above-mentioned preparation method comprises the following steps:

[0033] Step S10, mixing compound 1, methylamine hydrochloride, N,N-dimethylformamide and sodium bicarbonate to obtain compound 2;

[0034] Step S20, mixing compound 3, thionyl chloride and N,N-dimethylformamide to obtain compound 4;

[0035] Step S30, mixing compound 2, dichloromethane, an acid-binding agent and compound 4 to obtain a benzamide compound.

[0036] Specifically, first, compound 1, methylamine hydrochloride, N,N-dimethylformamide and sodium bicarbonate are mixed to prepare compound 2. Secondly, compound 3, thionyl chloride and N,N-dimethylformamide are mixed to prepare compound 4. Finally, compound 2, dichloromethane, an acid-binding agent and compound 4 are mixed to prepare a benzamide compound.

[0037] N,N-dimethylformamide is known as the "universal solvent" and has the advantages of wide solubility, aproticity, reactivity, stability, and low toxicity.

[0038] In this embodiment, N,N-dimethylformamide is selected as the solvent for compound 1 and compound 3, which can stabilize the reaction and provide convenient conditions for the synthesis of compound 2 and compound 4. It also has the characteristic of low toxicity. The acid-binding agent forms a salt with the generated hydrochloric acid to adjust the pH value of the solution.

[0039] In some embodiments of the present invention, the acid binding agent is pyridine. The chemical formula of pyridine is C 5 H 5N, is a six-membered heterocyclic compound containing a nitrogen atom, and the unshared electron pair on the nitrogen atom can accept a proton and exhibit alkalinity. In this embodiment, pyridine can combine with a strong acid to form a stable salt.

[0040] like Figure 3 As shown, in some embodiments of the present invention, the above-mentioned compound 1, methylamine hydrochloride, N,N-dimethylformamide and sodium bicarbonate are mixed to obtain compound 2, comprising:

[0041] Step S11, adding compound 1, methylamine hydrochloride and N,N-dimethylformamide into a container in sequence, mixing and stirring to obtain a second mixture;

[0042] Step S12, adding sodium bicarbonate to the second mixture, stirring for a first preset time, and filtering to obtain compound 2.

[0043] In this embodiment, the addition of sodium bicarbonate can adjust the pH value in the reaction system.

[0044] In some embodiments of the present invention, sodium bicarbonate is added in batches in step S120. That is, sodium bicarbonate is divided into multiple portions, and the next portion of sodium bicarbonate is added after the sodium bicarbonate added in the previous portion reacts completely. Depending on the amount of sodium bicarbonate used, it can be any integer number of 2, 3, 5, etc.

[0045] In this embodiment, adding sodium bicarbonate in batches can effectively prevent the generation of a large number of bubbles by adding too much sodium bicarbonate at one time, thereby controlling the intensity of the reaction.

[0046] like Figure 4 As shown, in some embodiments of the present invention, the above-mentioned compound 2, dichloromethane, pyridine and compound 4 are mixed to obtain a benzamide compound, including:

[0047] Step S31, adding compound 2, dichloromethane and pyridine into a container in sequence, mixing and stirring to obtain a third mixture;

[0048] Step S32, dissolving compound 4 in dichloromethane to obtain a fourth mixed solution;

[0049] Step S33, slowly dripping the fourth mixed solution into the third mixed solution, stirring for a second preset time, pouring into ice water, cooling and filtering to obtain a benzamide compound.

[0050] In this embodiment, dichloromethane is first used to dissolve compound 2 and compound 4 into a third mixed solution and a fourth mixed solution, respectively, and then the fourth mixed solution is slowly added dropwise to the third mixed solution, so that the reaction rates of compound 2 and compound 4 are uniform and the reaction is sufficient, thereby improving the yield of the benzamide compound.

[0051] In some embodiments of the present invention, the molar ratio of compound 1, methylamine hydrochloride and N,N-dimethylformamide is 0.8-1.5:8-15:8-15.

[0052] In some embodiments of the present invention, the molar ratio of compound 3 to thionyl chloride is 0.8-1.5:25-37.

[0053] In some embodiments of the present invention, the molar ratio of compound 2, compound 4 and pyridine is 0.8-1.5:1.0-1.5:4-7.

[0054] The present invention is specifically explained below using several embodiments, and the technical solutions in the embodiments of the present invention are clearly and completely described. The described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments.

[0055] Example 1

[0056] A preparation process of a benzamide compound, the specific steps are as follows:

[0057] Step S110, weigh 14.92 g of compound 1, 30.0 g of methylamine hydrochloride and 58.4 g of N,N-dimethylformamide, add them into a container in sequence, mix and stir to obtain a second mixture.

[0058] Step S120, adding 67.2 g of sodium bicarbonate into the second mixture in four portions, stirring for a first preset time of 72 h after the addition of sodium bicarbonate, and filtering to obtain compound 2.

[0059] Step S130, 29.05 g of compound 3, 357 g of thionyl chloride and 365 g of N,N-dimethylformamide were mixed and stirred for 48 h. After the reaction was complete, the excess thionyl chloride was removed by rotation to obtain compound 4;

[0060] Step S140, weighing 37.1 g of compound 2 and 79 g of pyridine, dissolving them in 100 ml of dichloromethane, mixing and stirring to obtain a third mixture;

[0061] Step S150, weighing 74.16 g of compound 4 and dissolving it in 100 ml of dichloromethane to obtain a fourth mixed solution;

[0062] Step S160, slowly dripping the fourth mixed solution into the third mixed solution, stirring for 96 hours, pouring into ice water, cooling and filtering to obtain a benzamide compound.

[0063] Example 2

[0064] A preparation process of a benzamide compound, the specific steps are as follows:

[0065] Step S210, weigh 14.92 g of compound 1, 56.25 g of methylamine hydrochloride and 109.5 g of N,N-dimethylformamide, add them into a container in sequence, mix and stir to obtain a second mixture.

[0066] Step S220, adding 126 g of sodium bicarbonate into the second mixture in four portions, stirring for a first preset time of 60 h after the addition of sodium bicarbonate, and filtering to obtain compound 2.

[0067] Step S230, 29.05 g of compound 3, 416.5 g of thionyl chloride and 438 g of N,N-dimethylformamide were mixed and stirred for 36 h. After the reaction was complete, the excess thionyl chloride was removed by rotation to obtain compound 4;

[0068] Step S240, weighing 37.1 g of compound 2 and 63.2 g of pyridine, dissolving them in 100 ml of dichloromethane, mixing and stirring to obtain a third mixture;

[0069] Step S250, weighing 61.8 g of compound 4 and dissolving it in 100 ml of dichloromethane to obtain a fourth mixed solution;

[0070] Step S260, slowly dripping the fourth mixed solution into the third mixed solution, stirring for 84 hours, pouring into ice water, cooling and filtering to obtain a benzamide compound.

[0071] Example 3

[0072] A preparation process of a benzamide compound, the specific steps are as follows:

[0073] Step S310, weigh 14.92 g of compound 1, 30.0 g of methylamine hydrochloride and 58.4 g of N,N-dimethylformamide, add them into a container in sequence, mix and stir to obtain a second mixture.

[0074] Step S320, adding 67.2 g of sodium bicarbonate into the second mixture in four portions, stirring for a first preset time of 84 h after the addition of sodium bicarbonate, and filtering to obtain compound 2.

[0075] Step S330, 29.05 g of compound 3, 357 g of thionyl chloride and 730.0 g of N,N-dimethylformamide were mixed and stirred for 60 h. After the reaction was complete, the excess thionyl chloride was removed by rotation to obtain compound 4;

[0076] Step S340, weighing 37.1 g of compound 2 and 79 g of pyridine, dissolving them in 100 ml of dichloromethane, mixing and stirring to obtain a third mixture;

[0077] Step S350, weighing 74.16 g of compound 4 and dissolving it in 100 ml of dichloromethane to obtain a fourth mixed solution;

[0078] Step S360, slowly dripping the fourth mixed solution into the third mixed solution, stirring for 96 hours, pouring into ice water, cooling and filtering to obtain a benzamide compound.

[0079] At this point, those skilled in the art should recognize that, although multiple exemplary embodiments of the present invention have been shown and described in detail herein, many other variations or modifications that conform to the principles of the present invention can still be directly determined or derived based on the content disclosed in the present invention without departing from the spirit and scope of the present invention. Therefore, the scope of the present invention should be understood and recognized as covering all these other variations or modifications.

Claims

1. A novel benzamide compound, characterized in that: The benzamide compound is 4-chloro-2-(methylcarbamoyl)phenyl-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, and the specific structural formula is:

2. A method for preparing a novel benzamide compound, characterized in that: The steps include: Compound 1, methylamine hydrochloride, N,N-dimethylformamide and sodium bicarbonate are mixed to obtain compound 2; the structural formula of compound 1 is The structural formula of the compound 2 is Compound 3, thionyl chloride and N,N-dimethylformamide are mixed to obtain compound 4; the structural formula of compound 3 is The structural formula of compound 4 is Compound 2, dichloromethane, pyridine and compound 4 are mixed to obtain the benzamide compound.

3. The method for preparing the benzamide compound according to claim 2, characterized in that: The compound 1, methylamine hydrochloride, N,N-dimethylformamide and sodium bicarbonate are mixed to obtain compound 2, comprising: Adding compound 1, methylamine hydrochloride and N,N-dimethylformamide into a container in sequence, mixing and stirring to obtain a second mixture; Sodium bicarbonate is added to the second mixture, stirred for a first preset time, and filtered to obtain compound 2.

4. The method for preparing the benzamide compound according to claim 2, characterized in that: The compound 2, dichloromethane, pyridine and compound 4 are mixed to obtain the benzamide compound, including: Compound 2, dichloromethane and pyridine are sequentially added into a container, mixed and stirred to obtain a third mixture; Dissolving compound 4 in dichloromethane to obtain a fourth mixed solution; The fourth mixed solution is slowly dripped into the third mixed solution, and after stirring for a second preset time, ice water is poured into the solution, and the solution is cooled and filtered to obtain the benzamide compound.

5. The method for preparing the benzamide compound according to claim 2, characterized in that: The molar ratio of the compound 1, methylamine hydrochloride and N,N-dimethylformamide is 0.8-1.5:8-15:8-15.

6. The method for preparing the benzamide compound according to claim 2, characterized in that: The molar ratio of the compound 3 to the thionyl chloride is 0.8-1.5:25-37.

7. The method for preparing the benzamide compound according to claim 2, characterized in that: The molar ratio of the compound 2, the compound 4 and pyridine is 0.8-1.5:1.0-1.5:4-7.

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