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Synthesis method of 2-formyl-4-carboxylic acid ethyl thiazole

A technology for the synthesis of ethyl thiazole carboxylate, which is applied in the chemical and pharmaceutical fields, can solve the problems of poor economy, complicated operation, and high production cost, and achieve the effects of low cost, high chemical purity, and short synthetic route

Pending Publication Date: 2019-11-08
苏州汉德创宏生化科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing preparation methods are complicated to operate, and column purification and crystalliza

Method used

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  • Synthesis method of 2-formyl-4-carboxylic acid ethyl thiazole
  • Synthesis method of 2-formyl-4-carboxylic acid ethyl thiazole
  • Synthesis method of 2-formyl-4-carboxylic acid ethyl thiazole

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Example Embodiment

[0032] Example 1

[0033] A synthetic method of 2-formyl-4-carboxylic acid ethyl thiazole, such as figure 1 As shown, including the following steps:

[0034] The first step is to react 2,2-dichloroacetic acid (1) with sodium ethoxide to produce sodium 2,2-diethoxy acetate (2):

[0035] Add the raw material 2,2-dichloroacetic acid (1) to the ethanol solution of sodium ethoxide, the molar ratio of 2,2-dichloroacetic acid (1) to sodium ethoxide is 1:3, and at 60-80 ℃, Stir for 2-3 h until the reaction is completed to obtain sodium 2,2-diethoxyacetate (2); the reaction solution is directly used in the next reaction without treatment.

[0036] The second step is to react sodium 2,2-diethoxy acetate (2) with an ethanol solution of hydrogen chloride to obtain ethyl 2,2-diethoxy acetate (3):

[0037] At 0-5 ℃, the ethanol solution of hydrogen chloride was added dropwise to the reaction solution of the first step, the molar ratio of hydrogen chloride to 2,2-diethoxy sodium acetate (2) was 1:1....

Example Embodiment

[0047] Example 2

[0048] A synthetic method of 2-formyl-4-carboxylic acid ethyl thiazole, such as figure 1 As shown, including the following steps:

[0049] The first step: reacting 2,2-dichloroacetic acid (1) with sodium ethoxide to produce sodium 2,2-diethoxyacetate (2);

[0050] The raw material 2,2-dichloroacetic acid (1) is added to the ethanol solution of sodium ethoxide, the molar ratio of 2,2-dichloroacetic acid (1) to sodium ethoxide is 1:3.5, and under the condition of 60-80 ℃, Stir for 2-3 h until the reaction is completed to obtain sodium 2,2-diethoxyacetate (2); the reaction solution is directly used in the next reaction without treatment.

[0051] The second step: reacting sodium 2,2-diethoxy acetate (2) with an ethanol solution of hydrogen chloride to obtain ethyl 2,2-diethoxy acetate (3);

[0052] Under the condition of 0-5℃, the ethanol solution of hydrogen chloride was added dropwise to the reaction solution of the first step. The molar ratio of hydrogen chloride to...

Example Embodiment

[0061] Example 3

[0062] A synthetic method of 2-formyl-4-carboxylic acid ethyl thiazole, such as figure 1 As shown, including the following steps:

[0063] The first step: reacting 2,2-dichloroacetic acid (1) with sodium ethoxide to produce sodium 2,2-diethoxyacetate (2);

[0064] Add the raw material 2,2-dichloroacetic acid (1) to the ethanol solution of sodium ethoxide, the molar ratio of 2,2-dichloroacetic acid (1) to sodium ethoxide is 1:4, and at 60-80 ℃, Stir for 2-3 h until the reaction is completed to obtain sodium 2,2-diethoxyacetate (2); the reaction solution is directly used in the next reaction without treatment.

[0065] The second step: reacting sodium 2,2-diethoxy acetate (2) with an ethanol solution of hydrogen chloride to obtain ethyl 2,2-diethoxy acetate (3);

[0066] At 0-5 ℃, the ethanol solution of hydrogen chloride was added dropwise to the reaction solution of the first step, the molar ratio of hydrogen chloride to 2,2-diethoxy sodium acetate (2) was 1:2.05; a...

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Abstract

The invention discloses a synthesis method of 2-formyl-4-carboxylic acid ethyl ester thiazole, the synthesis method takes dichloroacetic acid, sodium ethoxide and ethanol as initial raw materials to firstly synthesize 2,2-diethoxyacetic acid ethyl ester, then ammonia water is added to ammoniate to obtain 2,2-diethoxyacetamide, the 2,2-diethoxyacetamide is converted into 2,2-diethoxythioacetamide through thioation by use of a vulcanizing reagent, then the 2,2-diethoxythioacetamide is condensed with 3-ethyl bromopyruvate to generate 2-diethoxymethyl-4-carboxylic acid ethyl ester thiazole, and finally acid deprotection is performed in an acetone solution to obtain the 2-formyl-4-carboxylic acid ethyl ester thiazole. According to the synthesis method of the 2-formyl-4-carboxylic acid ethyl ester thiazole, and the used raw materials are low in price, high in safety and easy to obtain. In addition, the synthesis method has the advantages of short synthesis route, high yield, high chemical purity of the obtained product, no need of complicated operation, and large-scale production.

Description

technical field [0001] The invention belongs to the technical fields of medicine and chemical industry, and in particular relates to a method for synthesizing ethyl 2-formyl-4-carboxylate thiazole. Background technique [0002] As an important intermediate, thiazole has good biological activity and is widely used in the pesticide, chemical and pharmaceutical industries. It is often used as a pharmaceutical intermediate for structural modification, such as 2-formyl-4-carboxylic acid ethyl Esterthiazole. [0003] 2-Formyl-4-carboxylic acid ethyl thiazole has attracted wide attention because it is widely used in the synthesis of active drug molecules for the treatment of various diseases, and related reports have been received: PCT Int. APPl., 2018086139, Tetrahedron Letters, 57( 8), 920-923; 2016, Bioorganic & Medicinal Chemistry, 23(21), 6827-6843; 2015, Journal of Organic Chemistry, 80(8), 4184-4188; 2015, can be used to synthesize and treat malignant tumors, immune system ...

Claims

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Application Information

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IPC IPC(8): C07D277/56
CPCC07D277/56
Inventor 茅仲平马东旭陈广威
Owner 苏州汉德创宏生化科技有限公司
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