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Method for synthesizing carbamyl benzotriazole by three-component one-pot method

A technology of carbamoylbenzotriazole and benzotriazole, which is applied in the field of three-component one-pot synthesis of carbamoylbenzotriazole, which can solve the problems of difficult storage and difficult application in industrial production, and achieve high yield High, mild reaction conditions, high implementation value and potential socio-economic benefits

Inactive Publication Date: 2012-10-17
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is simple and easy to implement, but acyl azide is sensitive to acid, alkali, temperature, etc., it is not easy to store, and it is difficult to apply to industrial production

Method used

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  • Method for synthesizing carbamyl benzotriazole by three-component one-pot method
  • Method for synthesizing carbamyl benzotriazole by three-component one-pot method
  • Method for synthesizing carbamyl benzotriazole by three-component one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the preparation of N-phenylcarbamoylbenzotriazole

[0019] The amount ratio of feed material is benzoic acid: diphenylphosphoric azide: benzotriazole: catalyst=1.0: 1.0: 1.2: 2.0, wherein the consumption of benzoic acid is 10mmol, organic solvent is toluene, and its consumption is the quality of benzoic acid 20 times of that, the catalyst is triethylamine, and the reflux time is 6 hours.

[0020] In a 100mL round bottom flask equipped with a reflux condenser, add 1.22g (10mmol) of benzoic acid, 2.75g (10mmol) of diphenylphosphoryl azide, 1.43g (12mmol) of benzotriazole, and 2.02g of triethylamine ( 20mmol), toluene 24.4g, stirred under reflux for 6 hours, followed by TLC until the reaction of the raw materials was complete, after the reaction was complete, the solvent was removed under reduced pressure, dissolved in ethyl acetate, washed once with saturated sodium bicarbonate solution, and washed once with saturated sodium chloride solution , the organic ...

Embodiment 2

[0021] Embodiment 2: Preparation of N-phenylcarbamoylbenzotriazole

[0022] The amount ratio of the feed material is benzoic acid: diphenylphosphoric azide: benzotriazole: catalyst=1.0: 2.0: 1.2: 3.0, wherein the consumption of benzoic acid is 10mmol, the organic solvent is toluene, and the consumption is the quality of benzoic acid 30 times of that, the catalyst is triethylamine, and the reflux time is 4 hours.

[0023] Others are the same as in Example 1, the product is N-phenylcarbamoylbenzotriazole solid, and 1.55 g of the product is obtained, with a yield of 65% and a purity of 97.1%.

Embodiment 3

[0024] Embodiment 3: the preparation of N-phenylcarbamoylbenzotriazole

[0025] The amount ratio of the feed material is benzoic acid: diphenylphosphoric azide: benzotriazole: catalyst=1.0: 2.5: 1.2: 2.5, wherein the consumption of benzoic acid is 10mmol, the organic solvent is toluene, and the consumption is the quality of benzoic acid 20 times of that, the catalyst is triisopropylamine, and the reflux time is 5 hours.

[0026] Others are the same as in Example 1, the product is N-phenylcarbamoylbenzotriazole solid, and 1.50 g of the product is obtained, with a yield of 63% and a purity of 98.0%.

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Abstract

The invention discloses a method for synthesizing carbamyl benzotriazole by a three-component one-pot method. The method is characterized by taking organic carboxylic acid, diphenylphosphoryl azide and benzotriazole as raw materials and comprising the following steps of: under the effect of a catalyst, performing reflux reaction in toluene for 2-8 hours; performing after-treatment of the obtained reaction mixture; and recrystallizing in ethyl acetate to obtain carbamyl benzotriazole, wherein the substance amount ratio of the organic carboxylic acid to diphenylphosphoryl azide to benzotriazole to catalyst is 1.0:(1.0-3.0):(1.0-1.5):(1.5-3.0). The raw materials are simple and easily available, the price is low, the conditions are mild, the operation is simple and convenient, the yield is relatively high, the after-treatment is relatively convenient, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a chemical preparation method, in particular to a three-component one-pot method for synthesizing carbamoylbenzotriazole. Background technique [0002] Carbamoylbenzotriazole derivatives are an important class of organic heterocyclic compounds with important physiological activities and important applications in medicine and biology. Patent (Patent No. WO2007045393) reports that carbamoylbenzotriazole derivatives can be used as lipase and phospholipase inhibitors. [0003] Currently, there are many synthetic methods for carbamoylbenzotriazole derivatives. In the patent WO2007045393, it is reported that carbamoylbenzotriazoles are prepared by reacting various substituted benzotriazoles with amino acid chlorides or isocyanates. Although this method has a high yield, it is highly polluting to the environment, and its raw material isocyanate is highly toxic and sensitive to water, acid, alkali, etc. Christopher John Perry, Keith...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/18
Inventor 王小霞毛会
Owner ZHEJIANG NORMAL UNIVERSITY
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