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Method for preparing 1,2,3-thiadiazole-4-carboxylic acid

A technology of thiadiazole and dicarboxylic acid, which is applied in the field of compound synthesis, can solve the problems that the synthesis process cannot be enlarged and industrialized, and the synthesis rate is low, and achieve the effect of low price, high synthesis rate and easy availability of raw materials

Active Publication Date: 2016-12-14
安徽赛迪生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are certain defects in the above four synthetic routes. First, the synthetic rate is low. For example, the synthetic rate of 1 and 2 synthetic routes is only about 20%. In addition, the synthetic process cannot be enlarged for industrial production.

Method used

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  • Method for preparing 1,2,3-thiadiazole-4-carboxylic acid
  • Method for preparing 1,2,3-thiadiazole-4-carboxylic acid
  • Method for preparing 1,2,3-thiadiazole-4-carboxylic acid

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Embodiment 1

[0020] Into a 10L four-necked flask, add diaminomaleic cyanide: 410g, THF: 3.79L, triethylamine: 1.718kg, cool down to 0°C and slowly add thionyl chloride: 918.68g, dropwise, continue stirring After 6 hours, filter, wash the filter cake with THF, combine the washing liquid with the filtrate, spin dry (rotate to dryness), add 1.5 L of dichloroethane and 5 L of water, and steam distill to obtain 300 g of light yellow solid. Detection: HPLC 220nm 98%, yield of 4,5-dicyano-1,2,3-thiadiazole: 58.1%.

[0021] The reaction formula is:

[0022]

[0023] In a 2L four-neck flask, add water: 600g, slowly drop concentrated sulfuric acid: 600g, make 50% sulfuric acid aqueous solution, then add 4,5-dicyano-1,2,3-thiadiazole: 300g, React at 120°C for 12 hours, cool down to 0°C, stir for 2 hours, and filter to obtain 337.7g of white solid 1,2,3-thiadiazole 4,5-dicarboxylic acid, yield: 88%.

[0024] The reaction formula is:

[0025]

[0026] Put 250g of the white solid into a 500ml f...

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Abstract

The invention relates to a method for preparing 1,2,3-thiadiazole-4-carboxylic acid, which comprises: preparing 4,5-dicyano-1,2,3-thiadiazole by reaction between diaminomaleonitrile and dichloroethane; preparing 1,2,3-thiadiazole 4,5-dicarboxylic acid by the cyan-hydrolysis of 4,5-dicyano-1,2,3-thiadiazole; and preparing 1,2,3-thiadiazole-4-carboxylic acid by the decarboxylation reaction of 1,2,3-thiadiazole 4,5-dicarboxylic acid. The provided process route is high in synthesis rate of the target product, moreover, the process route can be magnified, the raw materials can be easily obtained and are cheap, and industrial production can be carried out.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for preparing 1,2,3-thiadiazole-4-carboxylic acid. Background technique [0002] There are mainly four known production routes of 1,2,3-thiadiazole-4-carboxylic acid as follows: [0003] [0004] There are certain defects in the above four synthetic routes. Firstly, the synthetic rate is low. For example, the synthetic rate of 1 and 2 synthetic routes is only about 20%. In addition, the synthetic process cannot be scaled up for industrial production. Contents of the invention [0005] The object of the present invention is to provide a method for preparing 1,2,3-thiadiazole-4-carboxylic acid, the synthesis rate of the target product is high, and the process route can be enlarged. [0006] To achieve the above object, the present invention adopts the following technical solutions: [0007] A method for preparing 1,2,3-thiadiazole-4-carboxylic acid, comprising the ...

Claims

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Application Information

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IPC IPC(8): C07D285/06
CPCC07D285/06
Inventor 魏晓延贺鹰魏巍余利灯
Owner 安徽赛迪生物科技股份有限公司
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