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Preparation method of 2-(2-thienyl)ethyl 4-methylbenzenesulfonate

A technology of p-toluenesulfonate and thiophenethanol, which is applied in the direction of organic chemistry, can solve the problems of unsuitability for industrial production, long reaction time, and low yield, and achieve the effects of low production cost, increased reaction speed, and reduced cost

Inactive Publication Date: 2013-10-23
HEILONGJIANG FUHE HUAXING PHARMA GROUP
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Problems solved by technology

In the prior art, 2-(2-thiophene) ethanol p-toluenesulfonate is mainly prepared by reacting 2-thiophene ethanol with p-toluenesulfonyl chloride. U.S. Patent US0225320 discloses that the above-mentioned reaction is carried out in toluene solvent, and in the reaction Add triethylamine as acid-binding agent, and react at 30 DEG C for 30 hours, the reaction time is longer, and at higher temperature for a long time, 2-(2-thiophene) ethanol p-toluenesulfonate is easily hydrolyzed, resulting in lower yield low, so it is not suitable for industrial production

Method used

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  • Preparation method of 2-(2-thienyl)ethyl 4-methylbenzenesulfonate

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Embodiment 1

[0013] Add 400 mL of dichloromethane and 163.2 g (0.85 mol) of p-toluenesulfonyl chloride to the dry reaction flask, stir and dissolve at room temperature; add 100 g (0.78 mol) of 2-thiophene ethanol and 8 g (0.14 mol) of potassium hydroxide to the above solution , Then add 130g of triethylamine, stir at room temperature for 2 hours, the filtered reaction solution was washed with saturated brine (200mL×3), and the organic phase was concentrated and dried to obtain 205g of 2-(2-thiophene)ethanol p-toluenesulfonate. The rate is 96%.

Embodiment 2

[0015] Add 1L of dichloromethane and 408g (2.12mol) of p-toluenesulfonyl chloride to the dry reaction flask, stir to dissolve at room temperature; add 250g (1.95mol) of 2-thiophene ethanol and 20g (0.35mol) of potassium hydroxide to the above solution, Then add 325g of triethylamine, stir at room temperature for 2 hours, the filtered reaction solution was washed with saturated brine (500mL×3), and the organic phase was concentrated and dried to obtain 506g of 2-(2-thiophene)ethanol p-toluenesulfonate. Yield 95%.

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Abstract

The invention relates to a preparation method of 2-(2-thienyl)ethyl 4-methylbenzenesulfonate. The 2-(2-thienyl)ethyl 4-methylbenzenesulfonate is synthesized through esterification reaction between 2-(2-thienyl)ethanol and paratoluensulfonyl chloride particularly under the potassium hydroxide catalysis condition. The esterification reaction is catalyzed by potassium hydroxide, so that the esterification reaction speed is greatly increased, and the reaction can be completely ended within only 2-3h. In addition, the yield of a target product obtained by the invention is larger than 85%, and particularly, the yield of the target product can be up to 96% when the potassium hydroxide is used as a catalyst. The preparation method provided by the invention is low in production cost, suitable for industrial production and also beneficial to the reduction of cost of down-stream clopidogrel products.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing 2-(2-thiophene) ethanol p-toluenesulfonate. Background technique [0002] 2-(2-thiophene) ethanol p-toluenesulfonate is an important intermediate in the synthesis of clopidogrel, the molecular formula is C 13 H 14 O 3 S 2 , The molecular weight is 282.38, and the structural formula is: [0003] [0004] Clopidogrel is a new type of highly effective antiplatelet aggregation drug, which is widely used clinically to treat and prevent myocardial infarction, cardiovascular and cerebrovascular diseases, etc., and its annual usage worldwide is huge. Therefore, the process of clopidogrel is improved and optimized Has a very important meaning. In the prior art, 2-(2-thiophene)ethanol p-toluenesulfonate is mainly prepared by the reaction of 2-thiopheneethanol and p-toluenesulfonyl chloride. US Patent No. US0225320 discloses that the above-mentioned rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/16
Inventor 吴光彦
Owner HEILONGJIANG FUHE HUAXING PHARMA GROUP
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