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Method for preparing 2-benzothiazole substituted aniline compound under catalysis of copper compound

A technology for benzothiazole and catalytic preparation, applied in directions such as organic chemistry, can solve problems such as unfavorable mass production, environmental pollution, inconvenience in operation, etc., and achieve the effects of easy operation, simple reaction operation and mild conditions

Active Publication Date: 2021-01-19
GUANGZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In the prior art, there are fewer types of reaction substrates for the synthesis of 2-benzothiazole-substituted aniline derivatives, and the conditions are relatively harsh. Sometimes it is necessary to use 2-aminobenzenethiol with an unpleasant odor as a raw material, which pollutes the environment and is inconvenient to operate. , not suitable for mass production, so it is very necessary and significant to develop a new, efficient, easy-to-operate, and readily available method for the synthesis of 2-benzothiazole-substituted aniline derivatives

Method used

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  • Method for preparing 2-benzothiazole substituted aniline compound under catalysis of copper compound
  • Method for preparing 2-benzothiazole substituted aniline compound under catalysis of copper compound
  • Method for preparing 2-benzothiazole substituted aniline compound under catalysis of copper compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1: 2-(Benzo[d]thiazol-2-yl)aniline

[0061] 221mg (1.5mmol) indole-2,3-dione, 219mg (1mmol) 2-iodoaniline, 256mg (1mmol) elemental sulfur (S8), 19mg (0.1mmol) catalyst CuI, 415mg (3mmol) K 2 CO 3 and 3mL solvent dimethyl sulfoxide (DMSO) were added to a 30mL sealed tube under air. Then the sealed tube was placed in an oil bath at 140° C. for 2 h under nitrogen atmosphere. After the reaction was finished, the reaction solution was cooled to room temperature, 80 mL of ethyl acetate was added, and the column chromatography (ethyl acetate was used as eluent) combined the organic layers, and the organic layers were washed with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was reduced to After pressure distillation, it was separated by silica gel column chromatography (ethyl acetate: petroleum ether = 1:20 as eluent) to obtain 176 mg of yellow solid with a yield of 78%.

[0062] The various characterization data of the resulting product are...

Embodiment 2

[0068] Example 2: 2-(Benzo[d]thiazol-2-yl)-4-methylaniline

[0069] 242mg (1.5mmol) 5-methylindole-2,3-dione, 219mg (1mmol) 2-iodoaniline, 256mg (1mmol) elemental sulfur (S8), 19mg (0.1mmol) catalyst CuI, 415mg (3mmol) )K 2 CO 3 and 3mL solvent dimethyl sulfoxide (DMSO) were added to a 30mL sealed tube under air. Then the sealed tube was placed in an oil bath at 140° C. for 2 h under nitrogen atmosphere. After the reaction was finished, the reaction solution was cooled to room temperature, 80 mL of ethyl acetate was added, and the column chromatography (ethyl acetate was used as eluent) combined the organic layers, and the organic layers were washed with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was reduced to After pressure distillation, it was separated by silica gel column chromatography (ethyl acetate: petroleum ether = 1:20 as eluent) to obtain 192 mg of a yellow solid with a yield of 80%.

[0070] The various characterization data of the ...

Embodiment 3

[0076] Example 3: 2-(Benzo[d]thiazol-2-yl)-4-methoxyaniline

[0077] With 266mg (1.5mmol) 5-methoxyindole-2,3-dione, 219mg (1mmol) 2-iodoaniline, 256mg (1mmol) elemental sulfur (S8), 19mg (0.1mmol) catalyst CuI, 415mg ( 3mmol) K 2 CO 3 and 3mL solvent dimethyl sulfoxide (DMSO) were added to a 30mL sealed tube under air. Then the sealed tube was placed in an oil bath at 140° C. for 2 h under nitrogen atmosphere. After the reaction was finished, the reaction solution was cooled to room temperature, 80 mL of ethyl acetate was added, and the column chromatography (ethyl acetate was used as eluent) combined the organic layers, and the organic layers were washed with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was reduced to After pressure distillation, it was separated by silica gel column chromatography (ethyl acetate: petroleum ether = 1:20 as eluent) to obtain 195 mg of a yellow solid with a yield of 76%.

[0078] The various characterization data ...

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Abstract

The invention belongs to the field of organic synthesis and metal catalysis, and discloses a method for preparing a 2-benzothiazole substituted aniline compound through catalysis of a copper compound.According to the invention, elemental sulfur which is cheap, easy to obtain, low in toxicity, easy to operate, stable and odorless is used as a sulfur source, commercially available isatin derivatives and 2-iodobenzidine are used as raw materials, and a series of 2-benzothiazole substituted aniline compounds are obtained at high yield through a cascade reaction under the catalytic action of a copper compound; 2-aminophenylmercaptan with unpleasant odor is prevented from being used as a raw material, and the invention has the advantages of simple reaction operation, mild conditions, easily available raw materials, short synthesis route and the like.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and metal catalysis, and in particular relates to a method for preparing 2-benzothiazole-substituted aniline compounds by catalyzing copper compounds. Background technique [0002] 2-substituted benzothiazole derivatives have wide application value in chemical industry, medicine, agriculture and other fields. Due to its good biological activity, it is widely used as an important matrix and lead framework in the creation of pesticides, medicines and other drugs. In industry, it can also be used as rubber vulcanization accelerator, plastic dyeing agent, etc. Recent studies have shown that 2-benzothiazole-substituted aniline compounds have very good practical value and can be used to synthesize a series of novel fluorescent probes, as shown in formula 1 below. Therefore, it is very necessary to develop a method for the synthesis of 2-benzothiazole-substituted aniline derivatives, which has receive...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66
CPCC07D277/66
Inventor 刘吉旦江锦源杨圳科郑李垚何芝洲王玉飞
Owner GUANGZHOU UNIVERSITY
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