AU2016102195A4 - Furan propylamine drug intermediates 2-furan acrylic acid synthesis method - Google Patents
Furan propylamine drug intermediates 2-furan acrylic acid synthesis method Download PDFInfo
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- AU2016102195A4 AU2016102195A4 AU2016102195A AU2016102195A AU2016102195A4 AU 2016102195 A4 AU2016102195 A4 AU 2016102195A4 AU 2016102195 A AU2016102195 A AU 2016102195A AU 2016102195 A AU2016102195 A AU 2016102195A AU 2016102195 A4 AU2016102195 A4 AU 2016102195A4
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Abstract
Furan propylamine drug intermediates 2-furan acrylic acid synthesis method comprises the following steps: equipped with a stiffer and a reflux condenser, a reaction vessel was added 3. 1mol 2-chloro-furan-methanol solution, 3.6--3.9 mol malonic acid solution (3), 300ml nitroethane solution, control stirred speed for 130--170rpm, the solution temperature is raised to 70 - 75 C, refluxed for 5--8 h, the temperature of the solution is reduced to 8 -- 13 C, added 310ml sodium bromide solution, 200ml solution of potassium hydrogen sulfite, control the reaction time to 90-120 min, standing for 3- 6 h, the precipitated solid was filtered, washed with salt solution, washed with toluene solution, washed with ethylenediamine solution, dehydrated with dehydrating agent, recrystallized in propionitrile solution, ultimately got 2-furyl acrylic acid crystals.
Description
Furan propylamine drug intermediates 2-furan acrylic acid synthesis method
TECHNICAL FIELD
The present invention relates to Furan propylamine drug intermediates 2-furan acrylic acid synthesis method.
BACKGROUND ART
Furan propylamine indications are primarily for schistosomiasis, it can also be used for fasciolopsiasis, the product is nitrofurans antimony-agent oral anti-schistosomiasis drug, it has the effect of interfering schistosome glucose metabolism, body muscle and chuck it loss of function, it flow into the liver with the blood and is surrounded disappear. It has specific cooling effect for the acute schistosomiasis patients, but poor efficacy alone. It has rapid oral absorption, and is mainly absorbed in the intestine. 2-furan acrylic acid as furan propylamine drug intermediates, its synthesis method is of great economic significance for improving drug synthesis product quality, reducing the by-product content.
SUMMARY OF THE INVENTION
Object of the present invention is to provide furan propylamine drug intermediates 2-furan acrylic acid synthesis method, comprising the following steps: (i) equipped with a stirrer and a reflux condenser, a reaction vessel was added 3.1mol 2-chloro-furan-methanol solution, 3.6-3.9 mol malonic acid solution (3), 300ml nitroethane solution, control stirred speed for 130—170rpm, the solution temperature is raised to 70-75 °C, refluxed for 5—8 h, the temperature of the solution is reduced to 8—13 °C, added 310ml sodium bromide solution, 200ml solution of potassium hydrogen sulfite, control the reaction time to 90-120 min, standing for 3-6 h, the precipitated solid was filtered, washed with salt solution, washed with toluene solution, washed with ethylenediamine solution, dehydrated with dehydrating agent, recrystallized in propionitrile solution, ultimately got 2-furyl acrylic acid crystals (1); wherein the 2-chloro-furan-methanol solution in step (i) has a mass fraction of 70—76%, the malonic acid solution in step (i) has a mass fraction of 80—87%,nitroethane solution in step (i) has a mass fraction of 60- -66%, sodium bromide solution in step (i) has a mass fraction of 30—35%, solution of potassium hydrogen sulfite in step (i) has a mass fraction of 40—45%; salt solution in step (i) is any one kind of ammonium bromide solution or potassium iodide solution, toluene solution in step (i) has a mass fraction of 70—75%, ethylenediamine solution in step (i) has a mass fraction of 85—90%, dehydrating agent in step (i) is any one kind of activated alumina or anhydrous sodium carbonate; propionitrile solution in step (i) has a mass fraction of 91— 98%.
The throughout reaction process can be summarized using the following reaction formula:
Advantage of the present invention is that: the reaction intermediate links are reduced, reducing the reaction temperature and reaction time, improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION
Embodiment 1
Equipped with a stirrer and a reflux condenser, a reaction vessel was added 3.1 mol 2-chloro-furan-methanol solution with a mass fraction of 70%, 3.6 mol malonic acid solution (3) with a mass fraction of 80%, 300ml nitroethane solution with a mass fraction of 60%, control stirred speed for 130 rpm, the solution temperature is raised to 70 °C, refluxed for 5 h, the temperature of the solution is reduced to 8°C, added 310ml sodium bromide solution, 200ml solution of potassium hydrogen sulfite with a mass fraction of 40%, control the reaction time to 90 min, standing for 3 h, the precipitated solid was filtered, washed with salt solution, washed with toluene solution with a mass fraction of 70%, washed with ethylenediamine solution with a mass fraction of 85%, dehydrated with activated alumina dehydrating agent, recrystallized in propionitrile solution with a mass fraction of 91%, ultimately got 2-furyl acrylic acid crystals 355.07g, yield 83%.
Embodiment 2
Equipped with a stirrer and a reflux condenser, a reaction vessel was added 3.1 mol 2-chloro-furan-methanol solution with a mass fraction of 73%, 3.8 mol malonic acid solution (3) with a mass fraction of 82%, 300ml nitroethane solution with a mass fraction of 63%, control stirred speed for 140 rpm, the solution temperature is raised to 72 °C, refluxed for 6 h, the temperature of the solution is reduced to 10°C, added 310ml sodium bromide solution with a mass fraction of 32%, 200ml solution of potassium hydrogen sulfite with a mass fraction of 42%, control the reaction time to 110 min, standing for 5 h, the precipitated solid was filtered, washed with potassium iodide solution, washed with toluene solution with a mass fraction of 72%, washed with ethylenediamine solution with a mass fraction of 87%, dehydrated with anhydrous sodium carbonate dehydrating agent, recrystallized in propionitrile solution with a mass fraction of 97%, ultimately got 2-furyl acrylic acid crystals 367.91g , yield 86%.
Embodiment 3
Equipped with a stirrer and a reflux condenser, a reaction vessel was added 3.1 mol 2-chloro-furan-methanol solution with a mass fraction of 76%, 3.9 mol malonic acid solution (3) with a mass fraction of 87%, 300ml nitroethane solution with a mass fraction of 66%, control stirred speed for 170 rpm, the solution temperature is raised to 75 °C, refluxed for 8 h, the temperature of the solution is reduced to 13°C, added 310ml sodium bromide solution with a mass fraction of 35%, 200ml solution of potassium hydrogen sulfite with a mass fraction of 45%, control the reaction time to 120 min, standing for 6 h, the precipitated solid was filtered, washed with ammonium bromide solution, washed with toluene solution with a mass fraction of 75%, washed with ethylenediamine solution with a mass fraction of 90%, dehydrated with activated alumina dehydrating agent, recrystallized in propionitrile solution with a mass fraction of 98%, ultimately got 2-furyl acrylic acid crystals 389.30g , yield 91%.
While a number of preferred embodiments have been described, it will be appreciated by persons skilled in the art that numerous variations and/or modifications may be made to the invention without departing from the spirit or scope of the invention as broadly described. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive.
Claims (4)
1. Furan propylamine drug intermediates 2-furan acrylic acid synthesis method, comprises the following steps: (i) equipped with a stirrer and a reflux condenser, a reaction vessel was added 3.1mol 2-chloro-furan-methanol solution, 3.6-3.9 mol malonic acid solution (3), 300ml nitroethane solution, control stirred speed for 130—170rpm, the solution temperature is raised to 70 - 75 °C, refluxed for 5—8 h, the temperature of the solution is reduced to 8 — 13 °C, added 310ml sodium bromide solution, 200ml solution of potassium hydrogen sulfite, control the reaction time to 90-120 min, standing for 3- 6 h, the precipitated solid was filtered, washed with salt solution, washed with toluene solution, washed with ethylenediamine solution, dehydrated with dehydrating agent, recrystallized in propionitrile solution, ultimately got 2-furyl acrylic acid crystals (1); wherein the 2-chloro-furan-methanol solution in step (i) has a mass fraction of 70—76%, the malonic acid solution in step (i) has a mass fraction of 80—87%,nitroethane solution in step (i) has a mass fraction of 60- -66%, sodium bromide solution in step (i) has a mass fraction of 30—35%,solution of potassium hydrogen sulfite in step (i) has a mass fraction of 40—45%; salt solution in step (i) is any one kind of ammonium bromide solution or potassium iodide solution, toluene solution in step (i) has a mass fraction of 70—75%.
2. Furan propylamine drug intermediates 2-furan acrylic acid synthesis method according to claim 1 wherein ethylenediamine solution in step (i) has a mass fraction of 85—90%.
3. Furan propylamine drug intermediates 2-furan acrylic acid synthesis method according to claim 1 wherein dehydrating agent in step (i) is any one kind of activated alumina or anhydrous sodium carbonate.
4. Furan propylamine drug intermediates 2-furan acrylic acid synthesis method according to claim 1 wherein propionitrile solution in step (i) has a mass fraction of 91— 98%.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2015109817417 | 2015-12-23 | ||
| CN201510981741.7A CN105439996A (en) | 2015-12-23 | 2015-12-23 | Synthesis method of furapromide drug intermediate 2-furfuracrylic acid |
| CN2016108241397 | 2016-09-17 | ||
| CN201610824139.7A CN106397375A (en) | 2015-12-23 | 2016-09-17 | Synthesis method of furpromide drug intermediate 2-furanacrylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2016102195A4 true AU2016102195A4 (en) | 2017-02-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016102195A Ceased AU2016102195A4 (en) | 2015-12-23 | 2016-12-23 | Furan propylamine drug intermediates 2-furan acrylic acid synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2016102195A4 (en) |
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2016
- 2016-12-23 AU AU2016102195A patent/AU2016102195A4/en not_active Ceased
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| FGI | Letters patent sealed or granted (innovation patent) | ||
| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |