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

A technology for p-toluenesulfonic acid ester and p-toluenesulfonyl chloride is applied in the field of preparing 2-ethanol p-toluenesulfonic acid ester, which can solve the problems of being unsuitable for industrial production, long reaction time, low yield and the like, and is suitable for industrial production. , The effect of low production cost and high yield

Active Publication Date: 2012-05-09
山东立新制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] U.S. Patent US2007 / 0225320 discloses that the above reaction is carried out in a toluene solvent, and triethylamine is added as an acid-binding agent during the reaction. The reaction needs to be carried out at a temperature of 30° C. for 30 hours, and the reaction time is long. , 2-(2-thienyl) ethanol p-toluenesulfonate is easily hydrolyzed, resulting in lower yield, so this method is not suitable for suitability for industrialized production

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

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Embodiment 1

[0015] According to the preparation method of 2-(2-thienyl) ethanol p-toluenesulfonate of the present embodiment, comprises the steps:

[0016] First, add 400 mL of toluene and 163.2 g (0.85 mol) p-toluenesulfonyl chloride into a dry and clean reaction flask, stir to dissolve the p-toluenesulfonyl chloride, and obtain a toluene solution of p-toluenesulfonyl chloride;

[0017] Next, cool the toluene solution of the obtained p-toluenesulfonyl chloride to 5° C., add 100 g (0.78 mol) of thiophene-2-ethanol and 9.5 g (0.078 mol) of N, N-dimethylaminopyridine (DMAP), and then add 130g of triethylamine was stirred at room temperature for 2h to obtain a mixed solution containing 2-(2-thienyl)ethanol p-toluenesulfonate;

[0018] Finally, use a Buchner funnel to filter the above mixed solution, rinse with 2×100mL of toluene, wash the resulting filtrate with 5×200mL of water, discard the water layer, and distill the organic layer under reduced pressure (distillation temperature does not ...

Embodiment 2

[0020] According to the preparation method of 2-(2-thienyl) ethanol p-toluenesulfonate of the present embodiment, comprises the steps:

[0021] First, add 400 mL of toluene and 163.2 g (0.85 mol) p-toluenesulfonyl chloride into a dry and clean reaction flask, stir to dissolve the p-toluenesulfonyl chloride, and obtain a toluene solution of p-toluenesulfonyl chloride;

[0022] Next, cool the toluene solution of the obtained p-toluenesulfonyl chloride to 5° C., add 100 g (0.78 mol) of thiophene-2-ethanol and 4.8 g (0.04 mol) of N, N-dimethylaminopyridine (DMAP), and then add 130g of triethylamine was stirred at room temperature for 2h to obtain a mixed solution containing 2-(2-thienyl)ethanol p-toluenesulfonate;

[0023] Finally, use a Buchner funnel to filter the above mixed solution, rinse with 2×100mL of toluene, wash the resulting filtrate with 5×200mL of water, discard the water layer, and distill the organic layer under reduced pressure (distillation temperature does not e...

Embodiment 3

[0025] According to the preparation method of 2-(2-thienyl) ethanol p-toluenesulfonate of the present embodiment, comprises the steps:

[0026] First, add 400 mL of toluene and 163.2 g (0.85 mol) p-toluenesulfonyl chloride into a dry and clean reaction flask, stir to dissolve the p-toluenesulfonyl chloride, and obtain a toluene solution of p-toluenesulfonyl chloride;

[0027] Next, the toluene solution of the obtained p-toluenesulfonyl chloride was cooled to 5° C., 100 g (0.78 mol) of thiophene-2-ethanol and 1.0 g (0.008 mol) of N, N-dimethylaminopyridine (DMAP) were added, and then Add 130g of triethylamine and stir at room temperature for 3h to obtain a mixed solution containing 2-(2-thienyl)ethanol p-toluenesulfonate;

[0028] Finally, use a Buchner funnel to filter the above mixed solution, rinse with 2×100mL of toluene, wash the resulting filtrate with 5×200mL of water, discard the water layer, and distill the organic layer under reduced pressure (distillation temperature...

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Abstract

The invention relates to a preparation method of 2-(2-thienyl) ethyl-4-methylbenzenesulfonate; which mainly uses thienyl-2-ethanol and p-toluenesulfonyl chloride for esterification reaction to synthesize 2-(2-thienyl) ethyl-4-methylbenzenesulfonate, and particularly, the esterification reaction is conducted in the existence of a pyridine catalyst. As the pyridine catalyst is used for catalyzing the esterification reaction, the speed of the esterification reaction is greatly improved; and with only 1.5 to 3 hours, the reaction can be completed. In addition, the method has high target product yield of more than 85 percent, and especially when N,N-dimethylaminopyridine are used as the catalyst, the target product yield can reach 98 percent. The preparation method has low production cost, andis applicable to industrialized production, and is beneficial to the cost reduction of downstream product, namely clopidogrel simultaneously.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for preparing 2-(2-thienyl)ethanol p-toluenesulfonate. Background technique [0002] 2-(2-Thienyl)ethanol p-toluenesulfonate is an important intermediate in the synthesis of the drug clopidogrel. Clopidogrel is a new type of highly effective anti-platelet aggregation drug, which has been widely used clinically in the treatment and prevention of myocardial infarction, cardiovascular and cerebrovascular diseases, etc. The annual global demand for clopidogrel is huge. Therefore, the improvement and optimization of the clopidogrel process is of great significance. In the prior art, 2-(2-thienyl)ethanol p-toluenesulfonate is mainly prepared by the reaction of thiophene-2-ethanol and p-toluenesulfonyl chloride, and its chemical equation is as follows: [0003] [0004] U.S. Patent US2007 / 0225320 discloses that the above reaction is carried out in a toluene solv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/16B01J31/02
Inventor 舒亮包志坚张爱青
Owner 山东立新制药有限公司