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Synthetic method of 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide

A technology of bromobenzamide and synthesis method, which is applied in the field of chemical synthesis, and can solve the problems of no ideal industrial production method, difficulty in treatment, backward technology, etc.

Inactive Publication Date: 2016-04-27
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 2-Amino-N, 3-dimethyl-4-chloro-5-bromobenzamide is an organic chemical intermediate, widely used in the synthesis of medicines and pesticides, and has a wide range of uses. There are dozens of pesticides synthesized with it The new fungicide produced has unique functions and is a promising fungicide and pesticide intermediate, but 2-amino-N,3-dimethyl-4-chloro-5-bromobenzyl There has been no ideal industrial production method for amides
The traditional production of 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide has backward technology, long process, low yield, large amount of three wastes, and is difficult to treat

Method used

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  • Synthetic method of 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide
  • Synthetic method of 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide

Examples

Experimental program
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Effect test

example 1

[0018] Add 100mL of tetrahydrofuran to a 250mL three-necked flask equipped with a thermometer, and then add 8g of methyl anthranilate, and stir and mix at 800r / min for 10min at 20°C; after the stirring and mixing are completed, slowly add 2g of bis(trichloromethyl)carbonate was stirred and reacted at 20°C, and at a speed of 1mL / s, slowly dropwise added a sodium hydroxide solution with a mass concentration of 25% into a three-necked flask, and continued to stir for 45min; After the stirring is completed, it is monitored by thin-layer chromatography. If the reaction is not completed, continue to stir until the reaction is completed. After the reaction is completed, continue to dropwise add a mass concentration of 25% sodium bicarbonate solution until the pH of the reaction solution is 8; After the adjustment is completed, weigh 20 g of an aqueous solution of methylamine with a mass concentration of 20% into a three-necked flask, stir and react for 30 minutes, then pass through ni...

example 2

[0020] Add 110mL of tetrahydrofuran to a 250mL three-necked flask equipped with a thermometer, and then add 9g of methyl anthranilate, and stir magnetically at a speed of 1000r / min for 12min at 25°C; after the stirring and mixing are completed, slowly add 2.5 g of bis(trichloromethyl)carbonate was stirred and reacted at 25°C, and a sodium hydroxide solution with a mass concentration of 25% was slowly dropped into a three-necked flask at a rate of 1 mL / s, and the stirring was continued for 52 min; After the stirring is completed, it is monitored by thin-layer chromatography. If the reaction is not completed, continue to stir until the reaction is completed. After the reaction is completed, continue to add dropwise a sodium bicarbonate solution with a mass concentration of 25% until the pH of the reaction solution is 8.5; After the pH adjustment is completed, weigh 22g of an aqueous solution of methylamine with a mass concentration of 20% into a three-necked flask, stir and react...

example 3

[0022]Add 120mL of tetrahydrofuran to a 250mL three-necked flask equipped with a thermometer, and then add 10g of methyl anthranilate, and stir and mix with a magnetic force at a speed of 1200r / min for 15min at 30°C; after the stirring and mixing are completed, slowly add 3g of bis(trichloromethyl)carbonate was stirred and reacted at 30°C, and at a speed of 1mL / s, slowly dropwise added a sodium hydroxide solution with a mass concentration of 25% into a three-necked flask, and continued to stir for 60min; After the stirring is completed, it is monitored by thin-layer chromatography. If the reaction is not completed, continue to stir until the reaction is completed. After the reaction is completed, continue to add dropwise a sodium bicarbonate solution with a mass concentration of 25% until the pH of the reaction solution is 9; After the adjustment is completed, weigh 25g of a 20% methylamine aqueous solution into a three-necked flask, stir and react for 45min, and then pass thro...

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Abstract

The invention relates to a synthetic method of 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide and belongs to the field of chemical synthesis. The method comprises the following steps: using tetrahydrofuran and tetrahydrofuran as raw materials to react under phosgene catalytic action, adjusting pH by dropwise adding a sodium bicarbonate solution, simultaneously carrying out a reaction between chlorosuccinimide, N-iodosuccinimide and N-bromosuccinimide, carrying out suction filtration, and oxidizing so as to prepare 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide. The method has advantages of simple operation and high synthesis rate.

Description

technical field [0001] The invention relates to a synthesis method of 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide, which belongs to the field of chemical synthesis. Background technique [0002] 2-Amino-N, 3-dimethyl-4-chloro-5-bromobenzamide is an organic chemical intermediate, widely used in the synthesis of medicines and pesticides, and has a wide range of uses. There are dozens of pesticides synthesized with it The new fungicide produced has unique functions and is a promising fungicide and pesticide intermediate, but 2-amino-N,3-dimethyl-4-chloro-5-bromobenzyl There has been no ideal industrial production method for amides. The traditional production of 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide has backward technology, long process, low yield, large amount of three wastes, and is difficult to treat. Contents of the invention [0003] The invention provides a method for synthesizing 2-amino-N,3-dimethyl-4-chloro-5-bromobenzamide with mild reaction conditions ...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/30
CPCC07C231/12C07C231/02C07D265/26C07C237/30
Inventor 董燕敏
Owner CHANGZHOU UNIV
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