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Synthesis method of furapromide drug intermediate 2-furfuracrylic acid

A technology of furan acrylic acid and furan propylamine, applied in directions such as organic chemistry, can solve problems such as poor curative effect, and achieve the effects of reducing intermediate links, improving reaction yield, reducing reaction temperature and reaction time

Inactive Publication Date: 2016-03-30
CHENGDU ZHONGHENG HUATIE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It has a specific antipyretic effect on patients with acute schistosomiasis, but the curative effect is poor when used alone

Method used

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  • Synthesis method of furapromide drug intermediate 2-furfuracrylic acid

Examples

Experimental program
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Effect test

example 1

[0011] In the reaction vessel that stirrer, reflux condenser are installed, adding mass fraction is 70% 2-furan chloromethanol solution (2) 3.1mol, mass fraction is 80% malonic acid solution (3) 3.6mol, mass fraction is 300ml of 60% nitroethane, control the stirring speed at 130rpm, increase the solution temperature to 70°C, reflux for 5h, lower the solution temperature to 8°C, add 310ml mass fraction of 30% sodium bromide solution, 200ml mass fraction of 40% sodium bromide solution Potassium bisulfate solution, reacted for 90min, stood still for 3h, precipitated solid, filtered, washed with ammonium bromide solution, the mass fraction was 70% toluene, 85% ethylenediamine was washed, activated alumina was dehydrated, and the mass fraction was Recrystallized from 91% acrylonitrile to obtain 355.07 g of crystal 2-furan acrylic acid, with a yield of 83%.

example 2

[0013] In the reaction vessel that agitator and reflux condenser are installed, adding mass fraction is 73% 2-furan chloromethanol solution (2) 3.1mol, mass fraction is 82% malonic acid solution (3) 3.8mol, mass fraction is 300ml of 63% nitroethane, control the stirring speed at 140rpm, increase the solution temperature to 72°C, reflux for 6h, lower the solution temperature to 10°C, add 310ml of 32% sodium bromide solution, and 200ml of 42% sodium bromide solution. Potassium bisulfate solution, reacted for 110min, stood still for 5h, precipitated solid, filtered, washed with potassium iodide solution, with mass fraction of 72% toluene, mass fraction of 87% ethylenediamine, anhydrous sodium carbonate dehydration, at mass fraction of 97% % acrylic acid was recrystallized to obtain 367.91 g of crystalline 2-furan acrylic acid, with a yield of 86%.

example 3

[0015] In the reaction vessel that agitator and reflux condenser are installed, adding mass fraction is 76% 2-furan chloromethanol solution (2) 3.1mol, mass fraction is 87% malonic acid solution (3) 3.9mol, mass fraction is 300ml of 66% nitroethane, control the stirring speed at 170rpm, increase the solution temperature to 75°C, reflux for 8h, lower the solution temperature to 13°C, add 310ml of 35% sodium bromide solution, and 200ml of 45% sodium bromide solution. Potassium bisulfate solution, reacted for 120min, stood still for 6h, precipitated solid, filtered, washed with ammonium bromide solution, the mass fraction was 75% toluene washing, the mass fraction was 90% ethylenediamine washing, activated alumina dehydration, the mass fraction was Recrystallized from 98% acrylonitrile to obtain 389.30 g of crystalline 2-furanacrylic acid, with a yield of 91%.

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Abstract

The invention relates to a synthesis method of a furapromide drug intermediate 2-furfuracrylic acid, which comprises the following steps: adding 3.1mol of 2-furylchloromethanol solution (2), 3.6-3.9mol of malonic acid solution (3) and 300ml of nitroethane into a reaction vessel which is provided with a stirrer and a reflux condenser, controlling the stirring rate at 130-170 rpm, heating the solution to 70-75 DEG C, refluxing for 5-8 hours, lowering the temperature of the solution to 8-13 DEG C, adding 310ml of sodium bromide solution and 200ml of potassium bisulfite solution, reacting for 90-120 minutes, standing for 3-6 hours, precipitating a solid, filtering, washing with a salt solution, washing with toluene, washing with ethylenediamine, dehydrating with a dehydrating agent, and recrystallizing in propionitrile to obtain the crystal 2-furfuracrylic acid.

Description

technical field [0001] The invention relates to a method for synthesizing 2-furanacrylic acid, a furanylamine drug intermediate. Background technique [0002] The indication of furanamide is mainly used for schistosomiasis japonicum, and can also be used for fascioliasis. This product is a nitrofuran non-antimony oral anti-schistosomiasis drug, which has the effect of interfering with the sugar metabolism of schistosomiasis, making its body muscles and suckers The function is lost, and it is surrounded and disappears with the blood flow into the liver. It has a specific antipyretic effect on patients with acute schistosomiasis, but the curative effect is poor when used alone. Oral absorption is rapid, mainly in the intestinal tract, most of which are quickly metabolized after entering the liver, the metabolites and the original drug are excreted in the urine, yellow furanamide and other metabolites can be detected in the urine within 15 minutes, and the excretion amount in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/54
CPCC07D307/54
Inventor 彭响亮
Owner CHENGDU ZHONGHENG HUATIE TECH CO LTD
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