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Method for synthesizing ticlopidine hydrochloride drug intermediate 2-nitryl vinyl thiophene

A technology of ticlopidine hydrochloride and nitroethylene, applied in the direction of organic chemistry, etc., can solve the problems of reducing the clearance rate, increasing the blood concentration of theophylline, the danger of overdose, etc., reducing intermediate links, reducing reaction temperature and Reaction time and effect of improving reaction yield

Inactive Publication Date: 2017-02-22
厦门莱恩斯特信息科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When this product is used in combination with theophylline, because it reduces the clearance rate of the latter, it will increase the blood concentration of theophylline and cause the risk of overdose

Method used

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  • Method for synthesizing ticlopidine hydrochloride drug intermediate 2-nitryl vinyl thiophene

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0012] In the reaction vessel that stirrer, thermometer, dropping funnel are installed, adding mass fraction is 55% thiophene methanediol solution (2) 1.3mol, and mass fraction is 65% nitromethane solution 1.6mol, 900ml of hexane, reduces Solution temperature to 3°C, control solution stirring speed 110rpm, react for 4h, raise solution temperature to 50°C, add 500ml of potassium bromide solution with a mass fraction of 30%, react for 3h, add 300ml of oxalic acid solution with a mass fraction of 40%, lower the solution Temperature to 10°C, react for 80min, lower the temperature to 2°C, let stand for 5h, precipitate solid, filter, wash with ammonium bromide solution, wash with 60% ethyl acetate, wash with 70% chlorobenzene, pentoxide Diphosphorus was dehydrated and recrystallized in 92% xylene to obtain 153.14 g of crystalline 2-nitrovinylthiophene with a yield of 76%.

example 2

[0014] In the reaction vessel that stirrer, thermometer, dropping funnel are installed, adding mass fraction is 57% thiophene methanediol solution (2) 1.3mol, and mass fraction is 67% nitromethane solution 1.7mol, 900ml of hexane, reduces Solution temperature to 4°C, control solution stirring speed 120rpm, react for 5h, increase solution temperature to 52°C, add 500ml of potassium bromide solution with a mass fraction of 32%, react for 4h, add 300ml of oxalic acid solution with a mass fraction of 42%, lower the solution Temperature to 12°C, react for 90min, lower the temperature to 3°C, stand for 6h, precipitate solid, filter, wash with sodium iodide solution, wash with 62% ethyl acetate, wash with 72% chlorobenzene, anhydrous Calcium sulfate was dehydrated and recrystallized in 93% xylene to obtain 163.22 g of crystalline 2-nitrovinylthiophene with a yield of 81%.

example 3

[0016] In the reaction vessel that stirrer, thermometer, dropping funnel are installed, adding mass fraction is 60% thiophene methanediol solution (2) 1.3mol, and mass fraction is 70% nitromethane solution 1.9mol, hexane 900ml, reduces Solution temperature to 7°C, control solution stirring speed 130rpm, react for 7h, increase solution temperature to 55°C, add 500ml of potassium bromide solution with a mass fraction of 35%, react for 5h, add 300ml of oxalic acid solution with a mass fraction of 45%, lower the solution Temperature to 16°C, react for 110min, lower the temperature to 5°C, stand still for 7h, precipitate solid, filter, wash with ammonium bromide solution, wash with 65% ethyl acetate, wash with 75% chlorobenzene, and pentoxide Diphosphorus was dehydrated and recrystallized in 96% xylene to obtain 169.26 g of crystal 2-nitrovinylthiophene with a yield of 84%.

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Abstract

The invention discloses a method for synthesizing a ticlopidine hydrochloride drug intermediate 2-nitryl vinyl thiophene. The method comprises the following steps: adding 1.3 mol of a thiophene methylene glycol solution, 1.6-1.9 mol of a nitromethane solution and 900ml of hexane into a reaction container in which a stirrer, a thermometer and a dropping funnel are mounted, reducing the temperature of the solution to be 3-7 DEG C, controlling the stirring speed of the solution to be 110-130rpm, performing a reaction for 4-7 hours, heating the solution to be 50-55 DEG C, adding 500ml of a potassium bromide solution, performing a reaction for 3-5 hours, adding 300ml of an oxalic acid solution, reducing the temperature of the solution to be 10-16 DEG C, performing a reaction for 80-110 minutes, reducing the temperature to be 2-5 DEG C, leaving to stand for 5-7 hours to separate out a solid, filtering, washing with a salt solution, washing with ethyl acetate, washing with chlorobenzene, dehydrating by using a dehydrant, and recrystallizing in dimethylbenzene, thereby obtaining the crystal 2-nitryl vinyl thiophene.

Description

technical field [0001] The invention relates to a method for synthesizing 2-nitrovinylthiophene, a pharmaceutical intermediate of ticlopidine hydrochloride. Background technique [0002] Ticlopidine hydrochloride is suitable for preventing thromboembolic diseases associated with cerebrovascular, cardiovascular and peripheral arteriosclerosis. These include first-episode and recurrent stroke, transient ischemic attack and loss of monocular vision, coronary heart disease and intermittent claudication, etc. It can also be used in cardiac surgery with cardiopulmonary bypass to prevent platelet loss, chronic kidney dialysis to increase the function of dialyzer . Combination of this product with any platelet aggregation inhibitors, thrombolytics and drugs that cause hypoprothrombinemia or thrombocytopenia can increase the risk of bleeding. If it is clinically necessary to use the drug in combination, close observation and laboratory monitoring should be carried out. When this p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/12
CPCC07D333/12
Inventor 彭响亮
Owner 厦门莱恩斯特信息科技有限公司