Method for synthesizing thiazolecarboxylic acid chemical intermediate key intermediate product

A synthesis method and technology of thiazole carboxylic acid, applied in the direction of organic chemistry, etc., can solve the problems of poor product yield and purity, difficult to meet the needs of biomedical synthesis, outdated, etc., and achieve high yield and purity, which is beneficial to industrialized mass production. Effect

Inactive Publication Date: 2018-08-24
南京聚科生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing synthesis method route of 5-ethoxy-1,2,4-thiadiazole-3-carboxylic acid is relatively conventional and old, resulting in poor yield and purity of the product, which is difficult to meet the synthesis needs of biomedicine

Method used

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  • Method for synthesizing thiazolecarboxylic acid chemical intermediate key intermediate product
  • Method for synthesizing thiazolecarboxylic acid chemical intermediate key intermediate product

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preparation example Construction

[0012] The synthetic method of key intermediate product of thiazole carboxylic acid chemical intermediate of the present invention, such as figure 1 As shown, it includes: (a) Mix ethyl cyanoformate, isopropyl ether and isopropanol, lower the temperature to -20°C to -5°C under the protection of an inert gas, and feed HCl gas under stirring conditions Carry out the reaction, let it stand to room temperature, and suction filter to obtain a white solid intermediate; (b) stir and mix water, sodium bicarbonate, ice and methyl tert-butyl ether, add the intermediate, and keep the water temperature below 0 ℃ and the pH is weakly alkaline to free the intermediate; separate the organic phase, dry and filter, and concentrate the filtrate under reduced pressure to obtain a transparent oily compound 2; (c) add the compound 2 to ethanol, under the protection of an inert gas Lower the temperature with an ice bath, add ammonium chloride to react; concentrate under reduced pressure to remove e...

Embodiment 1

[0015] This embodiment provides a kind of synthetic method of key intermediate product of thiazole carboxylic acid chemical intermediate, and it comprises:

[0016] (a) Add ethyl cyanoformate (100g, 1.0mol, 1.0eq), isopropyl ether (800ml) and isopropanol (67g, 1.1mmol, 1.1eq) in a 2L three-necked flask, 2 The temperature was lowered to -10°C under protection, and HCl gas was introduced to react for 15 hours under stirring, and allowed to stand at room temperature, and filtered with suction to obtain a white solid intermediate;

[0017] (b) Add 1L of water, 250g of sodium bicarbonate, 200g of ice, and 350mL of methyl tert-butyl ether into a 2L reaction flask. After stirring and mixing, add the above-mentioned intermediate while keeping the water temperature below 0°C and the pH at weakly alkaline (pH value is 8~9), dissociation completes (is about to disperse the intermediate in the above-mentioned mixture), separates the organic phase, 100L is extracted with methyl tert-butyl ...

Embodiment 2

[0020] This embodiment provides a synthetic method for key intermediates of thiazole carboxylic acid chemical intermediates, which is basically the same as in Example 1, except that in step (b), the organic phase is separated without methyl tert-butyl Extracted with base ether to obtain 104g of transparent oily liquid compound 2 (the yield of step a and step b is 68%, and the purity is 98.0%).

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Abstract

The invention relates to a method for synthesizing a thiazolecarboxylic acid chemical intermediate key intermediate product. The method comprises the steps that (a), cyanoformic ester, isopropyl etherand isopropyl alcohol are mixed, and the temperature is reduced to 20 DEG C-5 DEG C under the protection of inert gases; (b), water, sodium bicarbonate, ice and methyl tertiary butyl ether are stirred and mixed, an intermediate is added, and it is kept that the water temperature is less than 0 DEG C and the pH is alkalescence, so that the intermediate can be dissociated; (c), a chemical compound2 is added into ethyl alcohol, cooling is carried out through ice bath under the protection of inert gases, ammonium chloride is added to react, so that the chemical synthesis of 5-ethoxy-1,2,4-thiadiazole-3-carboxylate key intermediate can be achieved, the yield and purity are higher, and the method is conductive to industrialized quantity production.

Description

technical field [0001] The invention belongs to the field of fine chemical products and relates to a method for synthesizing key intermediates of thiazole carboxylic acid chemical intermediates. Background technique [0002] The CAS number of 5-ethoxy-1,2,4-thiadiazole-3-carboxylic acid is 67472-43-9, which belongs to fine chemical products; the density is 1.471g / cm 3 , the boiling point is 335.9°C at 760mmHg, the flash point is 156.9°C, and the refractive index is 1.573. The existing 5-ethoxy-1,2,4-thiadiazole-3-carboxylic acid synthesis method route is relatively conventional and old, resulting in poor yield and purity of the product, which is difficult to meet the synthesis needs of biomedicine. and It is the key intermediate product in the synthesis of 5-ethoxy-1,2,4-thiadiazole-3-carboxylic acid, and its synthetic preparation is for 5-ethoxy-1,2,4-thiadiazole-3-carboxylic acid The synthesis of acids plays a key role, so new synthetic routes need to be designed. Co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/14C07C257/06
CPCC07C257/14C07C257/06
Inventor 张红美
Owner 南京聚科生物科技有限公司
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