Preparation method of N-(1-phenylethyl) cyanamide and derivatives thereof

Abstract

The invention provides a preparation method of N-(1-phenylethyl) cyanamide and a derivative thereof, which comprises the following step of: reacting ethylbenzene or a derivative thereof with cyanamide under electrochemical catalysis to obtain the N-(1-phenylethyl) cyanamide and the derivative thereof. The N-(1-phenylethyl) cyanamide or the derivative thereof with higher additional value is obtained by performing electrochemical activation on aryl alkane and directly oxidizing the aryl alkane with selective C-H bonds, the raw materials are cheap and easy to obtain, the synthesis is simple, the production cost can be effectively reduced, the yield and the chemical selectivity can be improved, and the method is suitable for industrial production. The method can be conveniently applied to preparation of N-(1-phenylethyl) cyanamide and derivatives thereof, and has potential industrial application value.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic synthesis, and particularly relates to a method for preparing (1-phenylethyl) cyanamide and derivatives thereof N (RSC Adv., 2020, 10, 17288-17292). BACKGROUND

[0002] N- (1-phenylethyl) cyanamide and its derivatives have a variety of applications in industry, mainly including the following aspects: 1. Pesticide raw materials: a variety of pesticides, herbicides and other pesticide raw materials can be derived by chemical synthesis. 2. Pharmaceutical intermediates: can be used as pharmaceutical intermediates for the production of various drugs, such as antibiotics, analgesics, tumor drugs, etc. 3. Important chemical intermediates. Can be used as a multipurpose chemical intermediate to produce important chemical raw materials such as carboxylic acid, amide, etc., and can also be converted to synthesize natural heterocyclic compounds such as pyridine, imidazole, pyridazine, etc. 4. Important metal ligands, which are ligands for some important transition metals, widely used in transition metal catalysts, photochemical catalyst ligands, etc. In summary, N- (1-phenylethyl) cyanamide has wide application value in industry and can meet the different needs of multiple industries.

[0003] Due to the multiple uses of such compounds, the synthesis of N- (1-phenylethyl) cyanamide and its derivatives has become a hot topic, especially the establishment of simple and efficient synthesis of aromatic compounds based on alkyl aromatic hydrocarbons. N- The reported methods for synthesizing aromatic aldehydes or aromatic ketones and their derivatives mainly include the following: Using cyanamide and phenylboronic acid as raw materials, under the catalysis of copper acetate, using bipyridine as ligand and cesium carbonate as base, (1-phenylethyl) cyanamide and its derivatives can be efficiently synthesized in dichloromethane solvent. N- This conversion uses inexpensive copper as a catalyst, has good selectivity and high conversion rate, and has strong applicability. (Org. Lett. 2023, 25, 6446-6451) Using relatively inexpensive benzaldehyde as raw material, hydroxylamine as nitrogen source, sulfonyl fluoride as nucleophile and triethylamine as base, various N- (1-phenylethyl) cyanamide derivatives can be efficiently synthesized under the atmosphere. This method has strong substrate applicability and can react with various substituted aromatic aldehydes. (RSC Adv., 2020, 10, 17288-17292). A variety of (1-phenylethyl) cyanamide derivatives can be synthesized by using cyanobenzene as raw material, dichloromethane as solvent, hydroxylamine as nitrogen source, sulfonyl fluoride as nucleophile and sodium hydroxide as base. N- The method uses strong base, strong nucleophile and toxic gas, which is not conducive to industrial production. (Org. Biomol. Chem., 2019, 17, 7684-7688 A variety of (1-phenylethyl) cyanamide derivatives can be synthesized by using cyanobenzene as raw material, dichloromethane as solvent, hydroxylamine as nitrogen source, sulfonyl fluoride as nucleophile and sodium hydroxide as base. N-(1-phenylethyl) cyanamide The method has the advantages of wide substrate range, good selectivity, good yield, good functional group tolerance and simple operation, thereby providing a simple method for synthesizing (1-phenylethyl) cyanamide and its derivatives. (Synthetic Communications, 48:5, 500-510); N- The reaction of p-tolylmethyl oxime with TsCl under different conditions produces side reactions. 1.05 equivalents of TsCl and 1.05 equivalents of DIPEA are used in dichloromethane from 0°C to room temperature for 3h. (1-phenylethyl) cyanamide is obtained. The reaction conditions are mild and the substrate range is extensive. (Org. Lett. 2014, 16, 3, 892-895) N- In addition, a nucleophilic substitution reaction occurs between bromoacetonitrile and benzylamine to produce (1-phenylethyl) cyanamide. This reaction system is simple, but it requires toxic bromoacetonitrile, which greatly limits the application of the reaction. (Org. Biomol. Chem., 2012, 10, 2528-2533, Journal of the American Chemical Society (1960), 82, 1609-1613) N- This reaction can simply and efficiently synthesize (1-phenylethyl) cyanamide and its derivatives. N-（ (1-phenylethyl) cyanamide and its derivatives have a wide range of substrates, but there are still some shortcomings: the use of transition metal or noble metal catalysts to some extent causes the loss of noble metals and environmental pollution; the use of strong oxidizing agents increases the risk of the reaction to some extent; and some use toxic raw materials or catalysts, which limits the application of the reaction. SUMMARY

[0004] ​The embodiment of the present application aims to provide a kind of N- The present application provides a preparation method of (1-phenylethyl) cyanamide and derivatives thereof.

[0005] The embodiment of the present application is implemented in a kind of N- The present application provides a preparation method of (1-phenylethyl) cyanamide and derivatives thereof, comprising the following steps: under electrochemical catalysis, adding electrolyte, alkylbenzene is reacted with cyanamide source, (1-phenylethyl) cyanamide and derivatives thereof are obtained N- The present application provides a preparation method of (1-phenylethyl) cyanamide and derivatives thereof, comprising the following steps: under electrochemical catalysis, adding electrolyte, alkylbenzene is reacted with cyanamide source, (1-phenylethyl) cyanamide and derivatives thereof are obtained Optionally, the electrolyte of the above reaction is one or more of lithium perchlorate, ammonium perchlorate, tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium ethylbenzenesulfonate, tetrabutylammonium acetate.

[0006] Optionally, the electrolysis mode selected in the above reaction is one of constant current or constant voltage, and the constant voltage range is 0~30V, and the constant current range is 0~60mA.

[0007] Optionally, in the above reaction, the electrolyte is one or more of lithium perchlorate, ammonium perchlorate, tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium ethylbenzenesulfonate, tetrabutylammonium acetate. N-（ 1-phenylethyl) cyanamide and derivatives thereof R1, R2, group are each independently selected from one of hydrogen, halogen, substituted or unsubstituted C 1～10 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted C 1～10 alkoxy, substituted or unsubstituted amino, carboxyl, ester, acyl, cyano, nitro, hydroxyl, azido.

[0008] Optionally, in the above reaction, the molar ratio of ethylbenzene and its derivatives to cyanamide is 1:0.9~5.0.

[0009] Optionally, in the above reaction, the reaction is carried out in the presence of a solvent, and the solvent is one or more of water, methanol, ethanol, acetonitrile, benzene, toluene, tetrahydrofuran, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, hexafluoroisopropanol, trifluoroacetic acid, ethylene glycol, polyethylene glycol (PEG-200~600).

[0010] Optionally, in the above reaction, the reaction temperature is 0~60℃, and the reaction time is 1~24h.

[0011] Optionally, in the above reaction, the reaction is carried out in the presence of a solvent, and the solvent is one or more of water, methanol, ethanol, acetonitrile, benzene, toluene, tetrahydrofuran, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, ethylene glycol, polyethylene glycol (PEG-200~600).

[0012] Optionally, in the above reaction, the reaction is carried out under air or an inert atmosphere, and the inert atmosphere is a nitrogen atmosphere or an argon atmosphere.

[0013] Optionally, in the above reaction, the electrode is one or more of a platinum electrode, a nickel electrode, a graphite (net, rod, felt) electrode, a glassy carbon electrode, a copper electrode, a magnesium electrode, a silver electrode, an iron electrode, and a gold electrode.

[0014] Optionally, in the above reaction, the electrolytic cell is a double cell with a diaphragm or a single cell without a diaphragm.

[0015] Optionally, after the reaction, the reaction solution is extracted with ethyl acetate, washed with water multiple times, dried with anhydrous magnesium sulfate, and finally concentrated to obtain N- (1-phenylethyl) cyanamide and derivatives thereof. Optionally, the concentration is performed by one of normal pressure distillation, reduced pressure distillation, and rotary evaporation.

[0016] Post-treatment can also be performed by column chromatography purification, and the column chromatography uses 200-300 mesh silica gel as a separation resin, and at least one of petroleum ether, n-hexane, dichloromethane, water, acetonitrile, methanol, and ethyl acetate is selected as an eluent.

[0017] The N- The structure of (1-phenylethyl) cyanamide and derivatives thereof is as follows: The embodiment of the present application provides a kind of N- The preparation method of (1-phenylethyl) cyanamide and derivatives thereof directly realizes site-selective C-H bond cyanamide under mild reaction conditions through benzene ring positioning group, does not need other reagents, avoids the use of toxic metal catalyst and strong oxidizing agent at the same time, raw material is easy to obtain, can effectively reduce production cost, improve yield and chemical selectivity, can be conveniently applied to prepare various N- (1-phenylethyl) cyanamide and derivatives thereof. BRIEF DESCRIPTION OF DRAWINGS

[0018] Figure 1 The nuclear magnetic resonance spectrum of compound 3e provided in the embodiment 1 of the present application is as follows: 1 H NMR spectrum; Figure 2 The nuclear magnetic resonance spectrum of compound 3e prepared in the embodiment 1 of the present application is as follows: 13 C NMR spectrum.

[0019] Figure 3 The nuclear magnetic resonance spectrum of compound 3o provided in the embodiment 2 of the present application is as follows: 1 H NMR spectrum; Figure 4NMR of compound 3o prepared in Example 2 of this invention 13 C10 NMR spectrum.

[0020] Figure 5 NMR of compound 3ab provided in Example 3 of this invention 1 H NMR spectrum; Figure 6 NMR of compound 3ab prepared in Example 3 of this invention 13 C10 NMR spectrum.

[0021] Figure 7 NMR of compound 3ac provided in Example 4 of this invention 1 H NMR spectrum; Figure 8 NMR of compound 3ac prepared in Example 4 of this invention 13 C10 NMR spectrum.

[0022] Figure 9 NMR of compound 3ad provided in Example 5 of this invention 1 H NMR spectrum; Figure 10 NMR of compound 3ad prepared in Example 5 of this invention 13 C10 NMR spectrum. Detailed Implementation

[0023] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention.

[0024] The technical solutions and effects of the embodiments of the present invention will be further described in detail below with reference to the accompanying drawings.

[0025] This application provides a N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized by comprising the following steps: under electrochemical catalysis, adding a supporting electrolyte, reacting ethylbenzene and its derivatives with monocyanamide to obtain... N- (1-Phenylacetyl)cyanamide and its derivatives, the reaction formulas are as follows: R1, R2, and the radical are each independently selected from hydrogen, halogen, substituted or unsubstituted C. 1～10 Alkyl, substituted or unsubstituted aryl, substituted or unsubstituted C 1～10 One of alkoxy, substituted or unsubstituted amino, carboxyl, ester, acyl, cyano, nitro, hydroxy, and azide groups.

[0026] According to the application, the electrolyte is one or more of lithium perchlorate, ammonium perchlorate, tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium ethylbenzenesulfonate, tetrabutylammonium acetate. It should be understood that the common point of the above electrolytes in the reaction of the application is that they are ammonium salts or lithium salts, and all of them can create electrochemical catalytic electrolytic conditions in the reaction of the application. Therefore, as long as any of the above electrolytes is selected, the above reaction of the application can be realized. Although only some examples of the electrolytes are given in the embodiments of the application, it should be understood by those skilled in the art that the embodiments are only used to explain the preferred embodiments given by the application and are not used to limit the application. Those skilled in the art can also obtain the application according to other electrolytes given by the application under the inspiration of the embodiments.

[0027] According to the application, the molar ratio of ethylbenzene and its derivatives to monocyanoamine is 1:0.9-5.0. It should be understood that as long as ethylbenzene and its derivatives and monocyanoamine exist and electrochemical catalytic reaction conditions exist in the reaction of the application, the above reaction can occur. Although only some examples of the molar ratio of ethylbenzene and its derivatives to water are given in the embodiments of the application, it should be understood by those skilled in the art that the embodiments are only used to explain the preferred embodiments given by the application and are not used to limit the application. Those skilled in the art can also obtain the application according to other parameters given by the application under the inspiration of the embodiments.

[0028] According to the application, the solvent is one or more of water, methanol, ethanol, acetonitrile, benzene, toluene, tetrahydrofuran, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, hexafluoroisopropanol, trifluoroacetic acid, ethylene glycol, and polyethylene glycol. It should be understood that the above solvents are only used to dissolve the reactants in the reaction of the application, and the solvents themselves do not participate in the reaction. Therefore, as long as a solvent that can dissolve the reactants is selected, the above reaction of the application can be realized. Although only some examples of the above solvents as reaction solvents are given in the embodiments of the application, it should be understood by those skilled in the art that the embodiments are only used to explain the preferred embodiments given by the application and are not used to limit the application. Those skilled in the art can also obtain the application according to other solvents given by the application under the inspiration of the embodiments.

[0029] According to the application, the electrode of the electrochemical catalytic reactor is one or more of platinum electrode, nickel electrode, graphite electrode, glassy carbon electrode, copper electrode, magnesium electrode, silver electrode, iron electrode, and gold electrode. The electrolytic cell of the electrochemical catalytic reactor is one of a double cell separated by a diaphragm or a single cell without a diaphragm, or a continuous flow electrochemical reaction cell. The electrolytic mode of the electrochemical catalytic reaction is one of constant current or constant voltage, and the constant voltage is ≤30 V and the constant current is ≤60 mA.

[0030] The technical solutions and technical effects of the present application are further illustrated by specific examples.

[0031] Example 1 An amine N-（ The preparation method, structure and preparation method of 1-phenylethyl) cyanamide and its derivatives (compound 3e) are as follows: The specific steps are as follows: weigh monocyanoamine (0.4 mmol), ethyl biphenyl (0.2 mmol), tetrabutylammonium hexafluorophosphate (0.2 mmol), in a 10 mL reaction tube, add a magnet, use graphite as anode and cathode, replace with high-purity nitrogen gas for three times, then add dichloromethane (6 mL) into the flask under nitrogen protection, and react for 6 hours at room temperature under constant current electrolysis (10 mA). The reaction is tracked by TLC detection, after the reaction is completed, the flask is cooled to room temperature, 10 mL of saturated brine is added to the system, and the reaction is quenched by stirring; extract with ethyl acetate (10 mL x 3), combine the organic phases, and remove the solvent with a rotary evaporator to obtain the crude product; the crude product is loaded on silica gel, eluent is petroleum ether: ethyl acetate = 10:1 by volume, and column chromatography purification is carried out to obtain N- (4-biphenylmethyl) cyanamide, white solid, separation yield 90%.

[0032] Structure identification of compound 3e: Nuclear magnetic resonance data: 1H NMR (500 MHz, Chloroform-d) δ 7.64 – 7.59 (m, 4H), 7.49 – 7.42 (m,4H), 7.41 – 7.37 (m, 1H), 4.51 – 4.44 (m, 1H), 4.17 (s, 1H), 1.62 (d, J = 6.9Hz, 3H). 13C NMR (126 MHz, Chloroform-d) δ 141.35, 140.45, 140.38, 128.87,127.66, 127.56, 127.10, 126.63, 115.09, 55.39, 22.00. Structure identification of compound 3e: 1 H NMR, 13 C NMR as Figure 1 , as Figure 2 shown, the analysis results show that the target product obtained is correct.

[0033] Example 2 An amineN- The preparation method of (1-phenylethyl) cyanamide and its derivatives (compound 3o), their structure and preparation method are as follows: The specific steps are as follows: Weigh cyanamide (0.4 mmol), propylbiphenyl (0.2 mmol), and tetrabutylammonium tetrafluoroborate (0.2 mmol) into a 10 mL reaction tube. Add a magnetic stir bar, use graphite as the anode and cathode, and purge three times with high-purity nitrogen. Then, under nitrogen protection, add dichloromethane (6 mL) to the flask and react at room temperature with alternating polar constant current electrolysis (10 mA) for 6 hours. Monitor the reaction with TLC. After the reaction is complete, cool the flask to room temperature, add 10 mL of saturated saline solution to the system, and stir to quench the reaction. Extract with ethyl acetate (10 mL × 3), combine the organic phases, and remove the solvent using a rotary evaporator to obtain the crude product. The crude product is then purified by column chromatography on silica gel with petroleum ether:ethyl acetate at a volume ratio of 10:1 to obtain... N -(1-([1,1'-biphenyl]-4-yl)propyl)cyanamide, white solid, isolated yield 84%.

[0034] Structural identification of compound 3o: Nuclear magnetic resonance data: 1H NMR (500 MHz, Chloroform-d) δ 7.61 – 7.57 (m, 4H), 7.45 (t, J = 7.8 Hz, 2H), 7.39 – 7.33 (m, 3H), 4.23 (s, 1H), 4.16 – 4.10 (m, 1H), 2.03 – 1.83 (m, 2H), 0.94 (t, J = 7.4 Hz, 3H). 13C NMR (126 MHz, Chloroform-d) δ 141.34, 140.53, 139.19, 128.91,127.62, 127.58, 127.24, 127.15, 61.75, 29.00, 10.58. Compound 3o 1 H NMR, 13 The results of the 13C NMR data analysis indicate that the target product obtained is correct.

[0035] Example 3 A sort of N- The preparation method of (1-phenylethyl) cyanamide and its derivative (compound 3ab), its structure and preparation method are as follows: The specific steps are as follows: take monomethylamine (0.4 mmol), 4-(4-bromophenyl)ethylbenzene (0.2 mmol), tetrabutylammonium hexafluorophosphate (0.2 mmol), in a 10 mL reaction tube, add a magnet, use graphite as anode and cathode, replace three times with high-purity nitrogen, then add acetonitrile (6 mL) to the flask under nitrogen protection, and react at room temperature by alternating polarity constant current electrolysis (10 mA) for 6 hours. The reaction is tracked by TLC detection, after the reaction is completed, the flask is cooled to room temperature, 10 mL of saturated brine is added to the system, and the reaction is quenched by stirring; extract with ethyl acetate (10 mL x 3), combine the organic phases, and remove the solvent with a rotary evaporator to obtain the crude product; the crude product is loaded on silica gel, eluent is petroleum ether: ethyl acetate = 10:1 by volume, and column chromatography purification is carried out to obtain N -(1-(4'-bromo-[1,1'-biphenyl]-4-yl)ethyl)cyanamide, white solid, separation yield 91%. Structure identification of compound 3ab: Nuclear magnetic resonance data: 1H NMR (500 MHz, Chloroform-d)δ 7.57 – 7.51 (m, 4H), 7.43 – 7.37 (m,4H), 4.48 – 4.41 (m, 1H), 4.08 (s, 1H), 1.59 (d, J = 6.8 Hz, 3H). 13C NMR (126 MHz, Chloroform-d)δ 140.85, 140.23, 139.42, 132.08,128.76, 127.57, 126.86, 121.97, 115.01, 55.48, 22.12. Structure identification of compound 3ab 1 H NMR, 13 The analysis results of C NMR data show that the obtained target product is correct.

[0036] Example 4 A N- The preparation method, structure and preparation method of (1-phenylethyl) cyanamide and its derivatives (compound 3ac) are as follows: The specific steps are as follows: take cyanamide (0.4 mmol), 4-(4-bromophenyl) isopropylbenzene (0.2 mmol), tetrabutylammonium hexafluorophosphate (0.2 mmol), in a 10 mL reaction tube, add a magnet, use graphite as anode and cathode, replace with high-purity nitrogen three times, then add dichloromethane (6 mL) into the flask under nitrogen protection, and react at room temperature by alternating polarity constant current electrolysis (10 mA) for 6 hours. The reaction is tracked by TLC detection, after the reaction is completed, the flask is cooled to room temperature, 10 mL of saturated brine is added to the system, and the reaction is quenched by stirring; extract with ethyl acetate (10 mL x 3), combine the organic phases, and remove the solvent with a rotary evaporator to obtain the crude product; the crude product is loaded on silica gel, eluent is petroleum ether: ethyl acetate = 10:1 by volume, and column chromatography purification is carried out to obtain N-(2-([1,1'-biphenyl]-4-yl)propan-2-yl) cyanamide, white solid, separation yield 81%. The structure of compound 3ac is identified: The structure of compound 3z is identified: Nuclear magnetic resonance data: 1H NMR (500 MHz, Chloroform-d) δ 7.61 – 7.57 (m, 4H), 7.54 – 7.50 (m,2H), 7.47 – 7.43 (m, 2H), 7.39 – 7.34 (m, 1H), 4.36 (s, 1H), 1.69 (s, 6H). 13C NMR (126 MHz, Chloroform-d) δ 143.96, 140.58, 140.44, 128.91,127.57, 127.43, 127.13, 125.54, 114.70, 58.08, 29.40. The structure of compound 3ac is identified: 1 H NMR, 13 The results of C NMR data analysis show that the target product obtained is correct.

[0037] Example 5 A N- The preparation method, structure and preparation method of (1-phenylethyl) cyanamide and its derivatives (compound 3ad) are as follows: Take cyanamide (0.4 mmol), 4- (4-bromophenyl) isopropyl benzene (0.2 mmol), tetrabutylammonium hexafluorophosphate (0.2 mmol) in a 10 mL reaction tube, add a magnetic, use graphite as anode and cathode, replace three times with high-purity nitrogen, then add dichloromethane (6 mL) to the flask under nitrogen protection, and react at room temperature by alternating polarity constant current electrolysis (10 mA) for 6 hours. The reaction was tracked by TLC detection, and after the reaction was completed, the flask was cooled to room temperature, 10 mL of saturated brine was added to the system, and the reaction was quenched by stirring; extracted with ethyl acetate (10 mL x 3), combined the organic phase, and removed the solvent with a rotary evaporator to obtain the crude product; the crude product was loaded on silica gel, eluent was petroleum ether: ethyl acetate = 10: 1, and column chromatography purification was carried out to obtain N- (2- ( [1, 1'-biphenyl] -4-yl) propan-2-yl) cyanamide, white solid, separation yield 80%.

[0038] Structure identification of compound 3ad: Nuclear magnetic resonance data: 1H NMR (500 MHz, Chloroform-d) δ 7.61 – 7.58 (m, 2H), 7.56 – 7.50 (m,4H), 7.36 – 7.32 (m, 2H), 4.66 (s, 1H), 3.04 – 2.95 (m, 1H), 1.68 (s, 6H),1.34 (d, J = 7.0 Hz, 6H). 13C NMR (126 MHz, Chloroform-d) δ 148.23, 143.67, 140.36, 137.90,127.15, 126.98, 126.94, 125.43, 57.92, 33.80, 29.32, 24.00. Finally, it should be pointed out that: the above examples are only used to illustrate the technical solutions of the present application, but not to limit them; although the present application has been described in detail with reference to the foregoing examples, those skilled in the art should understand that they can still modify the technical solutions described in the foregoing examples, or make equivalent replacement for part or all of the technical features; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. A kind N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, Includes the following steps: Under electrochemical catalysis, with the addition of a supporting electrolyte, ethylbenzene and its derivatives are reacted with cyanamide to obtain... N- (1-Phenylacetyl)cyanamide and its derivatives, the reaction formulas are as follows:

2. As described in claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The electrolyte is one or more of lithium perchlorate, ammonium perchlorate, tetrabutyltetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetraethylbenzenesulfonate, and tetraethylammonium acetate.

3. As described in claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The electrolysis method selected in the electrochemical catalysis is either constant current or constant voltage, with constant voltage ≤30V and constant current ≤60mA.

4. As described in claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The N- In (1-phenylethyl) cyanamide and its derivatives, R1, R2, and the radicals are each independently selected from hydrogen, halogen, substituted or unsubstituted C. 1～10 Alkyl, substituted or unsubstituted aryl, substituted or unsubstituted C 1～10 One of alkoxy, substituted or unsubstituted amino, carboxyl, ester, acyl, cyano, nitro, hydroxy, and azide groups.

5. The method according to claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The molar ratio of ethylbenzene and its derivatives to cyanamide is 1:0.9~5.

0.

6. The method according to claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The reaction is carried out in the presence of a solvent, which is one or more of the following: water, methanol, ethanol, acetonitrile, benzene, toluene, tetrahydrofuran, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, hexafluoroisopropanol, trifluoroacetic acid, ethylene glycol, and polyethylene glycol.

7. The method according to claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The reaction is carried out in air or an inert atmosphere, wherein the inert atmosphere is a nitrogen atmosphere or an argon atmosphere.

8. The method according to claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The electrodes are one or more of the following: platinum electrode, nickel electrode, graphite electrode, glassy carbon electrode, copper electrode, magnesium electrode, silver electrode, iron electrode, and gold electrode.

9. The method according to claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, The selected electrolytic cell can be a dual cell separated by a diaphragm or a single cell without a diaphragm.

10. The benzene according to claim 1 N- A method for preparing (1-phenylethyl) cyanamide and its derivatives, characterized in that, After the reaction was completed, the reaction solution was extracted with ethyl acetate, washed multiple times with water using the organic phase, dried with anhydrous magnesium sulfate, and finally concentrated to obtain... N- (1-Phenylacetyl)cyanamide and its derivatives.

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