Method for preparing 4-methyl-2-sulfomethyl-1(3)H-imidazole

A technology of thiomethyl and methylisothiourea, which is applied in the field of synthesis of 4-methyl-2-thiomethyl-1H-imidazole, can solve the problems of difficult control of the reaction, inconvenient operation, and low synthesis yield. Achieve the effects of easy amplification, increased yield, and shortened synthetic routes

Inactive Publication Date: 2012-05-23
上海药明康德新药开发有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves technical problems such as low synthesis yield, the use of highly toxic raw materials, inconvenient operation, and difficult reaction control.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Example 1: Dissolve 150 mg (1.62 mmol) of chloroacetone in 5 mL of N,N-dimethylformamide (DMF), and then add 1.62 mmol of S-methylisothiourea (or its phase corresponding to the various salts), 448 mg (3.24 mmol) of K 2 CO 3 , 24 mg (0.16 mmol) of NaI, heated to 80°C, and stirred overnight (12-16 hours). Then the reaction solution was cooled, poured into ice water, extracted with ethyl acetate (100 ml*4), the organic phase was washed twice with saturated brine, the organic phase was combined, and anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated under reduced pressure to obtain 160 mg of crude 4-methyl-2-thiomethyl-1(3)H-imidazole, which was purified by column chromatography to obtain 148 mg of the product, yield: 71.2%.

Embodiment 2

[0010] Embodiment 2: 15 g (162 mmol) of chloroacetone are dissolved in 500 mL of DMF, and then 162 mmol of S-methylisothiourea (or its corresponding various salts) are added successively, 44.8 g (324 mmol ) of K 2 CO 3 , 2.4 g (16 mmol) of NaI, heated to 80°C, and stirred overnight. Then the reaction solution was cooled, poured into ice water, extracted with ethyl acetate (1000 ml*4), the organic phase was washed twice with saturated brine, the organic phase was combined, and anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated under reduced pressure to obtain 16.5 g of crude 4-methyl-2-thiomethyl-1(3)H-imidazole, which was purified by column chromatography to obtain 15 g of the product, yield: 72.1%.

Embodiment 3

[0011] Embodiment 3: the chloracetone of 150 g (1.62mol) is dissolved in the DMF of 5000 mL, then add the S-methylisothiourea (or its corresponding various salts) of 1.62 mol successively, 448 g (3.24 mol) of K 2 CO 3 , 24 g (0.16 mol) of NaI, heated to 80°C, and stirred overnight. Then the reaction solution was cooled, poured into ice water, extracted with ethyl acetate (10L*4), the organic phase was washed twice with saturated brine, the organic phase was combined, and anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated under reduced pressure to obtain 168 g of crude 4-methyl-2-thiomethyl-1(3)H-imidazole, which was purified by column chromatography to obtain 151 g of the product, yield: 72.5%.

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Abstract

The invention relates to a method for preparing 4-methyl-2-sulfomethyl-1(3)H-imidazole. The technical problems of long route, low yield, difficulty in control of reaction, inconvenience in experiment operation and the like in the traditional synthetic process are solved. S-methylisothiourea (or various corresponding salts) and chloroacetone are heated to be prepared into the 4-methyl-2-sulfomethyl-1(3)H-imidazole, wherein K2CO3 serves as alkali and N,N-dimethylformamide serves as a solvent. The reaction formula is shown in the specifications. The 4-methyl-2-sulfomethyl-1(3)H-imidazole prepared by the method is a useful intermediate or product for the synthesis of a plurality of medicaments.

Description

technical field [0001] The invention relates to a synthesis method of 4-methyl-2-thiomethyl-1(3)H-imidazole. Background technique [0002] 4-Methyl-2-thiomethyl-1(3)H-imidazole and related derivatives are widely used in medicinal chemistry and organic synthesis. The current synthetic method of 4-methyl-2-thiomethyl-1(3)H-imidazole [Journal of the Chemical Society; 1951; 3030, (Bullerwell; Lawson; Journal of the Chemical Society; 1951; 3030; DOI: 10.1039 4-methyl-2- Thiomethyl-1(3)H-imidazole. This synthesis method mainly has the following problems: (1) The reaction process uses highly toxic drugs, which makes the experimental operation inconvenient; (2) The polarity of the product is high, and the purification is difficult; (3) The alkylation reaction is not easy to control, and the yield low rate. Concrete reaction formula is as follows: [0003] [0004] Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/84
Inventor 孙继奎郭爱新耿春梅马建义姜鲁勇马汝建陈曙辉
Owner 上海药明康德新药开发有限公司
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