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Preparation method of 3-[(4-amido-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazol

A technology of methylthiazole and chloroethyl, applied in 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methyl The field of preparation of thiazole can solve the problem of not preparing chlorothiamine, and achieve the effects of simple preparation method, improved quality and mild reaction conditions

Active Publication Date: 2014-03-26
江西天新药业股份有限公司
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is currently no method for preparing chlorthiamine, let alone a method for vitamin B 1 High-purity chlorothiamine standard for the determination of chlorothiamine content in products

Method used

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  • Preparation method of 3-[(4-amido-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazol
  • Preparation method of 3-[(4-amido-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazol
  • Preparation method of 3-[(4-amido-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazol

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preparation example Construction

[0013] According to the present invention, the preparation method of said 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazole comprises: Under chlorination reaction conditions, in the presence of organic solvents, vitamin B 1 Contact with chlorinating agents.

[0014] Vitamin B 1 Also known as thiamine or anti-neurinflammator, vitamin B 1 Can exist in the form of hydrochloride or nitrate, vitamin B used for medicinal purposes 1 It generally exists in the form of hydrochloride, and its chemical formula is as follows:

[0015]

[0016] Wherein, the hydroxychlorination reaction refers to the vitamin B 1 In contact with chlorinating agents, vitamin B 1 The hydroxyl group in the hydroxyethyl group in the structure is replaced by the chlorine in the chlorinating agent.

[0017] According to the method of the present invention, for vitamin B 1 There is no particular limitation on the ratio of the amount of the chlorinating agent, generally, the chl...

Embodiment 1

[0032] Add 400ml of chloroform and 20g of vitamin B in a 500ml three-necked flask with a stirring device 1 , start stirring, and slowly add 48.3ml of thionyl chloride at room temperature (25°C, the same below). After feeding, continue to stir and react at room temperature for 5 hours. Evaporate chloroform and excess thionyl chloride under reduced pressure to obtain a white extract, then add 400ml of absolute ethanol, heat up to 40°C under stirring conditions, dissolve and clarify for 0.5 hours to obtain a transparent and clear liquid, stand still, Cool to crystallize, filter, wash the filter cake with 0°C cold absolute ethanol, and dry in vacuo to obtain 10.6 g of white solid.

Embodiment 2

[0034] It was prepared in the same manner as in Example 1, except that the amount of thionyl chloride was 5 ml, and the obtained white solid was 5.5 g.

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Abstract

The invention relates to a preparation method of 3-[(4-amido-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazol. The preparation method comprises the following step of contacting a vitamin B1 with a chlorinating agent under the condition of hydroxy chlorination reaction in the presence of an organic solvent. The preparation method of the 3-[(4-amido-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazol is simple, available in raw materials and mild in reaction condition; the obtained product is high in purity, provides the guarantee for the identification of a substance related to the vitamin B1 and provides the basis for improving and enhancing the quality of the vitamin B1 in production.

Description

technical field [0001] The invention relates to a vitamin B 1 The key related substance-3-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-5-(2-chloroethyl)-4-methylthiazole preparation method. Background technique [0002] 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-chloroethyl)-4-methylthiazole, also known as chlorothiamine, its English name is : {3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-chlor oethyl)-4-methyl-thiazolium(chlorothiamine)}, its structural formula is as follows: [0003] [0004] Chlorthiamine is used in the production of vitamin B 1 The key related substances produced during the process, the content of which directly affects the vitamin B 1 product quality. The European Pharmacopoeia has strict regulations on its content, and its effect on vitamin B is determined by the content of high-purity chlorthiamine. 1 The impact of the product is a must for high-end registration certification. However, there is currently no method for preparing chlorthia...

Claims

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Application Information

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IPC IPC(8): C07D415/00
CPCC07D415/00
Inventor 郭军袁道林徐志刚郭官安万真
Owner 江西天新药业股份有限公司
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