Synthetic method for intermediate diethyl diethylmalonate of barbiturate

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 increasing Cl influx and prolonging the opening time of chlorine channels To achieve the effect of increasing the reaction yield, reducing the reaction temperature and reaction time, and reducing the intermediate links

Inactive Publication Date: 2017-02-15
XIAMEN AN PU DUN INFORMATION TECH CO LTD
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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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  • Synthetic method for intermediate diethyl diethylmalonate of barbiturate

Examples

Experimental program
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Effect test

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

he invention provides a synthetic method for an intermediate, i.e., diethyl diethylmalonate, of barbiturate. The synthetic method comprises the following steps: adding 1.13 mol of ethanolamine and 0.5 mol of cuprous chloride into a reaction vessel and controlling a stirring speed to be 130 to 160 rpm; after complete dissolving of ethanolamine, adding 0.65 mol of diethyl malonate drop by drop within 2 to 3 h; heating a solution obtained in the previous step to 70 to 75 DEG C and maintaining the heating state for 50 to 70 min; carrying out cooling, wherein a solid is precipitated; then adding 1.1 to 1.3 mol of ethylamine drop by drop within 2 to 3 h and maintaining a reflux state for 4 to 5 h; adding 300 ml of a potassium chloride solution and decreasing the temperature of the solution to 5 to 8 DEG C; carrying out extraction with cyclohexane three to five times and combining extract; successively carrying out washing with a salt solution, dehydrating with a dehydrating agent and evaporation of cyclohexane; then carrying out pressure-reduced distillation and collecting a fraction obtained at a temperature of 185 to 195 DEG C; and subjecting the fraction to re-crystallization in acetonitrile so as to obtain a crystal, i.e., diethyl diethylmalonate; wherein the mass fraction of the potassium chloride solution is 15 to 20%, the mass fraction of cyclohexane is 80 to 85%, and the salt solution is any one selected from a group consisting 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): C07C67/31C07C69/708
CPCC07C67/31C07C69/708
Inventor 廖如佴
Owner XIAMEN AN PU DUN INFORMATION TECH CO LTD
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