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Synthesis method of barbitone drug intermediate diethyl diethylmalonate

A technology of diethyl malonate and synthesis method, which is applied in the field of synthesis of diethyl malonate, an intermediate of barbiturates, and can solve the problem of prolonging the opening time of chlorine channels and increasing the influx of Cl and other problems, to achieve the effect of reducing reaction temperature and reaction time, increasing reaction yield and reducing intermediate links

Inactive Publication Date: 2016-03-30
CHENGDU KA DI FU TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, unlike benzodiazepines, barbiturates increase Cl influx by prolonging the opening time of chlorine channels, causing hyperpolarization

Method used

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  • Synthesis method of barbitone drug intermediate diethyl diethylmalonate

Examples

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example 1

[0012] Add 1.13mol of ethanolamine (3) and 0.5mol of cuprous chloride into the reaction vessel, and control the stirring speed at 130rpm. After the ethanolamine is completely dissolved, add 0.65mol of diethyl malonate (2) dropwise, and the dropping time is controlled at 2h , raise the temperature of the solution to 70°C, maintain the heating state for 50 minutes, and solid precipitates after cooling, add 1.1 mol of ethylamine (4) dropwise, control the dropping time at 2 hours, keep the reflux state for 4 hours, and add 15% chloride by mass fraction Potassium solution 300ml, lower the temperature of the solution to 5°C, extract 3 times with cyclohexane, combine the extracts, wash with sodium nitrate solution, dehydrate with calcium sulfate, distill out cyclohexane, then distill under reduced pressure at 1.6kPa, collect at 185--195°C The diethyl diethyl malonate was recrystallized in 90% acetonitrile by mass fraction to obtain 120.74 g of crystalline diethyl malonate, with a yiel...

example 2

[0014] Add 1.13mol of ethanolamine (3) and 0.5mol of cuprous chloride into the reaction vessel, and control the stirring speed at 140rpm. After the ethanolamine is completely dissolved, add 0.65mol of diethyl malonate (2) dropwise, and the dropping time is controlled at 2h , raise the temperature of the solution to 72°C, maintain the heating state for 60 minutes, and solid precipitates after cooling, add 1.2 mol of ethylamine (4) dropwise, control the dropping time at 2 hours, keep the reflux state for 4 hours, add 17% chlorinated Potassium solution 300ml, lower the temperature of the solution to 7°C, extract 4 times with cyclohexane, combine the extracts, wash with potassium sulfate solution, dehydrate activated alumina, distill cyclohexane, and then distill under reduced pressure at 1.65kPa to collect 185--195 The fraction at ℃ was recrystallized in acetonitrile with a mass fraction of 925% to obtain 124.96 g of crystalline diethyl malonate, with a yield of 89%.

example 3

[0016] Add 1.13mol of ethanolamine (3) and 0.5mol of cuprous chloride to the reaction vessel, and control the stirring speed at 160rpm. After the ethanolamine is completely dissolved, add 0.65mol of diethyl malonate (2) dropwise, and the dropping time is controlled at 3h , Raise the temperature of the solution to 75°C, maintain the heating state for 70 minutes, and solid precipitates after cooling, add 1.3 mol of ethylamine (4) dropwise, control the dropping time at 3 hours, keep the reflux state for 5 hours, add 20% chlorinated Potassium solution 300ml, lower the solution temperature to 8°C, extract 5 times with cyclohexane with a mass fraction of 85%, combine the extracts, wash with sodium nitrate solution, dehydrate calcium sulfate, distill cyclohexane, then distill under reduced pressure at 1.7kPa, collect The fraction at 185--195°C was recrystallized in acetonitrile with a mass fraction of 95% to obtain 130.57 g of diethyl diethylmalonate in a yield of 93%.

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Abstract

The invention relates to a synthesis method of a barbitone drug intermediate diethyl diethylmalonate, which comprises the following steps: adding 1.13 mol of ethanolamine and 0.5 mol of cuprous chloride into a reaction vessel, controlling the stirring rate at 130-160 rpm until the ethanolamine is completely dissolved, dropwisely adding 0.65 mol of diethyl malonate within 2-3 hours, heating the solution to 70-75 DEG C, keeping the heating state for 50-70 minutes, cooling to precipitate a solid, dropwisely adding 1.1-1.3 mol of ethylamine within 2-3 hours, keeping the reflux state for 4-5 hours, adding 300ml of potassium chloride solution, cooling the solution to 5-8 DEG C, extracting with cyclohexane 3-5 times, merging the extracting solutions, washing with a salt solution, dehydrating with a dehydrating agent, distilling to remove the cyclohexane, distilling under reduced pressure, collecting the 185-195-DEG C fraction, and recrystallizing in acetonitrile to obtain the crystal diethyl diethylmalonate, wherein the mass percent of the potassium chloride solution is 15-20%, the mass percent of the cyclohexane is 80-85%, and the salt solution is any one of sodium nitrate and potassium sulfate.

Description

technical field [0001] The invention relates to a method for synthesizing barbiturate intermediate diethylmalonate. Background technique [0002] Barbiturates have sedative, hypnotic, anticonvulsant and antiepileptic effects. It can also be used as a pre-anesthesia drug, and when used in combination with antipyretic and analgesic drugs, it can enhance the analgesic effect of the latter. In recent years, it has been reported that this product can be used to prevent neonatal hyperbilirubinemia and kernicterus, and can also treat cholestasis. After adding phenobarbital to patients with cerebral edema, cerebral edema and herniation improved quickly, blood pressure was easily stabilized, and cerebral vasospasm and rebleeding were also reduced. Oral administration of this product combined with intramuscular injection of chorionic gonadotropin treats primary infertility. It can also treat polycystic ovum syndrome and reduce the incidence of intracranial hemorrhage in premature i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/708C07C67/31
CPCC07C67/31C07C69/708
Inventor 廖如佴
Owner CHENGDU KA DI FU TECH
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