Preparation method of 3-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-5-(2-sulfonyl oxy ethyl)-4-methylthiazole

A technology of sulfonyloxyethyl and methylthiazole, applied in the direction of organic chemistry and the like, can solve the problem of not preparing thiamine sulfate and the like, and achieve the effects of simple preparation method, mild reaction conditions and improved quality

Active Publication Date: 2012-07-11
江西天新药业股份有限公司
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  • Abstract
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  • Application Information

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Problems solved by technology

However, there is currently no method for preparing thiamine sulfate, let alone a method for vitamin B 1 High-purity Thiamine Sulfate Standards for Determination of Thiamine Sulfate Content in Products

Method used

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  • Preparation method of 3-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-5-(2-sulfonyl oxy ethyl)-4-methylthiazole
  • Preparation method of 3-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-5-(2-sulfonyl oxy ethyl)-4-methylthiazole
  • Preparation method of 3-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-5-(2-sulfonyl oxy ethyl)-4-methylthiazole

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preparation example Construction

[0012] According to the present invention, the preparation method of said 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-sulfonyloxyethyl)-4-methylthiazole comprises: Under the conditions of sulfation reaction, in the presence of organic solvent, vitamin B 1 Contact with sulfonating agents.

[0013] According to the method of the present invention, for vitamin B 1 The ratio of the amount of the sulfonating agent is not particularly limited, generally, the sulfonating agent is in excess, preferably, vitamin B 1 The molar ratio to the sulfonating agent is 1:1-20; more preferably, vitamin B 1 The molar ratio to the sulfonating agent is 1:5-15.

[0014] According to the method of the present invention, there is no particular limitation on the type of the sulfonating agent, it can be various sulfonating agents commonly used in the art, preferably, the sulfonating agent is selected from concentrated sulfuric acid, oleum, trioxide At least one of sulfur, sulfite, chlorosulfonic ...

Embodiment 1

[0025] Add 300ml of carbon tetrachloride and 20ml of chlorosulfonic acid into a 500ml three-necked flask with a stirring device, start stirring, stir at 60°C for 30min, and then add vitamin B into the flask 1 10.2 g, kept stirring at 60°C for 5 hours. Cool to room temperature (25°C), stand still for 30 minutes to separate layers, and decant the supernatant to obtain crude thiamine sulfate. Add 400ml of absolute ethanol, and stir for 30min at 15°C. After cooling and filtering, the filter cake was washed with cold ethanol at 0°C, and dried in vacuo to obtain 8.3 g of a white solid.

Embodiment 2

[0027] It was prepared in the same manner as in Example 1, except that the amount of chlorosulfonic acid was 10 ml, and 7.6 g of white solids were obtained.

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Abstract

The invention discloses a preparation method of 3-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-5-(2-sulfonyl oxy ethyl)-4-methylthiazole. The preparation method comprises the step that vitamin B1 is in contact with a sulfonating agent in the existence of an organic solvent under the condition of a sulfuric acid esterification reaction. By adopting the method disclosed by the invention, products with higher purity can be obtained; and besides, the preparation method is simple, reaction raw materials are easy to obtain, the reaction condition is wild and the reaction products are easy to separate and purify. The preparation method of the 3-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-5-(2-sulfonyl oxy ethyl)-4-methylthiazole, which is provided by the invention, has the advantages that a guarantee is provided for the identification of important related substances used during the production of the vitamin B1, and an evidence is provided for the improvement on the quality of the vitamin B1 in the production process at the same time.

Description

technical field [0001] The invention relates to a vitamin B 1 The preparation method of the key related substance-3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-sulfonyloxyethyl)-4-methylthiazole. Background technique [0002] 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-sulfonyloxyethyl)-4-methylthiazole, also known as thiamine sulfate, its English The name is: {3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(sulphonatooxy)ethyl]thiazolium(thiamine sulphate ester)}, and its structural formula is as follows: [0003] [0004] Thiamine sulfate is used in the preparation 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 thiamine sulfate 1 The impact of the product is a must for high-end registration certification. However, there...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06
Inventor 魏欣万真吴仁德刘标兵范大红
Owner 江西天新药业股份有限公司
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