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Synthetic method of etamsylate

A technology of sulfoethylamine and a synthesis method, which is applied in the field of pharmaceutical synthesis, can solve the problems of poor product quality, many by-products, low yield and the like, and achieves the effects of reducing production cost, reducing three-waste discharge and improving product yield

Active Publication Date: 2013-02-27
SHANDONG FANGMING PHARMACEUTICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The shortcoming of this technique is: because p-benzoquinone reacts incompletely, adds the solubility of phensulfame in water and ethanol is bigger, makes product yield low, generally no more than 40%, and p-benzoquinone price is higher, There are problems such as the absorption of tail gas when using sulfur dioxide
[0012] The disadvantages of this process are: excessive sulfuric acid is used as sulfonating agent in the synthesis process, subsequent separation and purification are difficult, there are many by-products, the yield is low (below 60%), three wastes are difficult to treat, the product quality is poor, and the cost is high

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0038] (1) Preparation of 2,5-dihydroxybenzenesulfonic acid

[0039] In a 500L reaction tank equipped with stirring, reflux condenser, and thermometer, add 50kg of hydroquinone and 150g of dichloroethane, start stirring, heat distillation and azeotropic dehydration until anhydrous, then cool down to 30°C, add chlorine dropwise 50kg of sulfonic acid was dropped within 3 hours, and the reaction was cooled with ice water, and the temperature was slowly raised to 90°C for 1 hour, then the temperature was lowered, dichloroethane was separated, and 36L of water was added to the residue to make 2,5-dihydroxy Benzenesulfonic acid is dissolved to obtain 2,5-dihydroxybenzenesulfonic acid solution;

[0040] (2) Preparation of the crude product of phensulfame

[0041] In a 500L reaction tank equipped with stirring, high-level tank, and thermometer, add the 2,5-dihydroxybenzenesulfonic acid solution obtained in step (1), add diethylamine into the high-level tank, and 2,5-dihydroxybenzenes...

Embodiment 2

[0046] (1) Preparation of 2,5-dihydroxybenzenesulfonic acid

[0047] In a 500L reaction tank equipped with stirring, reflux condenser, and thermometer, add 50kg of hydroquinone and 250g of dichloromethane, start stirring, heat distillation and azeotropic dehydration to anhydrous, then lower the temperature to 50°C, and add chlorosulfur dropwise Add 55kg of acid, drop it within 3 hours, and cool the reaction with ice water, react at 30°C for 3 hours, then lower the temperature, separate dichloroethane, add 40L of water to the residue, and dissolve 2,5-dihydroxybenzenesulfonic acid , to obtain 2,5-dihydroxybenzenesulfonic acid solution;

[0048] (2) Preparation of the crude product of phensulfame

[0049] In a 500L reaction tank equipped with stirring, high-level tank, and thermometer, add the 2,5-dihydroxybenzenesulfonic acid solution obtained in step (1), add diethylamine into the high-level tank, and 2,5-dihydroxybenzenesulfonic acid The mass ratio to diethylamine is 1:1, a...

Embodiment 3

[0054] (1) Preparation of 2,5-dihydroxybenzenesulfonic acid

[0055]In a 500L reaction tank equipped with stirring, reflux condenser, and thermometer, add 50kg of hydroquinone and 180g of chloroform, start stirring, heat distillation and azeotropic dehydration to anhydrous, then cool down to 40°C, and dropwise add 52kg of chlorosulfonic acid , dropped within 3 hours, and cooled the reaction with ice water, slowly raised the temperature to 50°C for 2 hours, then lowered the temperature, separated dichloroethane, and added 38L of water to the residue to make 2,5-dihydroxybenzenesulfonic acid Dissolving to obtain 2,5-dihydroxybenzenesulfonic acid solution;

[0056] (2) Preparation of the crude product of phensulfame

[0057] In a 500L reaction tank equipped with stirring, high-level tank, and thermometer, add the 2,5-dihydroxybenzenesulfonic acid solution obtained in step (1), add diethylamine into the high-level tank, and 2,5-dihydroxybenzenesulfonic acid The mass ratio to die...

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Abstract

The invention relates to a synthetic method of etamsylate. The synthetic method comprises the following steps of (1) preparation of 2,5-dihydroxybenzenesulfonic acid; (2) preparation of a etamsylate crude product; and (3) purification. Compared with a conventional synthetic process of the etamsylate adopting concentrated sulfuric acid as a sulfonating agent, the synthetic method has the following advantages that the synthetic method employs chlorosulfonic acid as the sulfonating agent, and performs azeotropic dehydration on benzenediol and an organic solvent until anhydrous before sulfonation to ensure that no water is in the reaction system, thereby increasing product yield; hydrogen chloride gas produced during the sulfonation process can be absorbed by water to make hydrochloric acid, thereby decreasing discharge of three wastes (waste gas, waste water and waste residues); and usage amount of the sulfonating agent is decreased during the sulfonation process, so that production cost is reduced.

Description

technical field [0001] The invention relates to a method for synthesizing phensulfame, which belongs to the technical field of drug synthesis. Background technique [0002] Ethylamine phensulfate (CAS: 2624-44-4), also known as Zhixuemin, its chemical name is 2,5-dihydroxybenzenesulfonic acid diethylamine salt, and its structural formula is: [0003] [0004] (1) [0005] Pharmacokinetic studies have shown that fensulfame can increase the number of platelets, enhance the aggregation and adhesion of platelets, and promote the release of coagulation active substances, thereby producing a hemostatic effect. Lasts for 4 to 6 hours. This product is suitable for the prevention and treatment of surgical bleeding, thrombocytopenic purpura or allergic purpura and bleeding caused by other reasons, such as cerebral hemorrhage, gastrointestinal bleeding, urinary tract bleeding, fundus bleeding, gum bleeding, epistaxis, etc. Combined with other hemostatic drugs such as aminomethylb...

Claims

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Application Information

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IPC IPC(8): C07C309/42C07C211/05C07C303/32C07C209/00
Inventor 范兴山王飞龙孙洋涛靳风会范纪超
Owner SHANDONG FANGMING PHARMACEUTICAL CO LTD
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