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Method for synthesizing oxiracetam intermediate 4-ethyl chloroacetoacetate

A technology for the synthesis of ethyl chloroacetoacetate, which is applied to the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, and can solve problems such as low product yield, decomposition loss of target products, and difficulties in separation and purification. Achieve the effect of high product purity, increase the probability of "collision" and low process cost

Active Publication Date: 2019-03-12
THE SECOND PEOPLES HOSPITAL OF SHENZHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This method product yield is on the low side, and reason is exactly that a certain amount of ethyl 2-chloroacetoacetate by-product can be generated in the reaction process, and this by-product is very close to 4-ethyl chloroacetoacetate physical property (as boiling point), causes separation Purification is difficult and often requires repeated rectification, resulting in the decomposition loss of the target product

Method used

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  • Method for synthesizing oxiracetam intermediate 4-ethyl chloroacetoacetate
  • Method for synthesizing oxiracetam intermediate 4-ethyl chloroacetoacetate
  • Method for synthesizing oxiracetam intermediate 4-ethyl chloroacetoacetate

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Embodiment 1

[0030] The synthetic method of ethyl 4-chloroacetoacetate, comprises the following steps:

[0031] 1) Mix the ethyl acetate, the catalyst and DMSO evenly, pass in argon, control the pressure to 4.8 atmospheres, control the temperature to 128°C, add the solution of ethyl chloroacetate and ethanol dropwise, and control the addition time to 21min; After finishing, raise the reaction temperature to 152° C., raise the pressure to 9 atmospheres, and then continue to react for 22 hours to complete the reaction;

[0032] The preparation method of the catalyst used is as follows: the molecular sieve of type 5A is soaked in 20% potassium carbonate aqueous solution for 50 hours, dried in the air, and then activated at 450 DEG C to obtain.

[0033] The consumption ratio of ethyl acetate and catalyzer is 1g:0.31g, the consumption ratio of ethyl acetate and DMSO is 1g:6.8ml, the consumption ratio of ethyl acetate and ethyl chloroacetate is 1mol:0.97mol, ethyl chloroacetate and The usage ra...

Embodiment 2

[0036] The synthetic method of ethyl 4-chloroacetoacetate, comprises the following steps:

[0037] 1) Mix ethyl acetate, catalyst and DMF, feed nitrogen, control the pressure to 3 atmospheres, control the temperature to 110°C, add the solution of methyl chloroacetate and methanol dropwise, and control the addition time to 15min; , raising the reaction temperature to 145°C, raising the pressure to 8 atmospheres, and then continuing to react for 15 hours to complete the reaction;

[0038] The preparation method of the catalyst is as follows: immerse the 4A type molecular sieve in 15% potassium carbonate or sodium carbonate aqueous solution for 2 days, then dry it, and then activate it at 350°C.

[0039] The consumption ratio of ethyl acetate and catalyzer is 1g:0.25g, and the consumption ratio of described ethyl acetate and DMF is 1g:5.6ml, and the consumption ratio of described ethyl acetate and methyl chloroacetate is 1mol:0.95mol, so The consumption ratio of methyl chloroace...

Embodiment 3

[0042] The synthetic method of ethyl 4-chloroacetoacetate, comprises the following steps:

[0043] 1) Mix the ethyl acetate, the catalyst and DMSO evenly, pass in argon, control the pressure to 5 atmospheres, control the temperature to 135°C, add the solution of ethyl chloroacetate and ethanol dropwise, and control the addition time to 25min; After finishing, raise the reaction temperature to 160° C., raise the pressure to 10 atmospheres, and then continue to react for 25 hours to complete the reaction;

[0044] The preparation method of the catalyst is as follows: immerse the 5A type molecular sieve in 25% potassium carbonate or sodium carbonate aqueous solution for 3 days, then dry it, and then activate it at 470 DEG C to obtain it.

[0045] The consumption ratio of ethyl acetate and catalyzer is 1g:0.33g, and the consumption ratio of described ethyl acetate and DMSO is 1g:7.5ml, and the consumption ratio of described ethyl acetate and ethyl chloroacetate is 1mol:1mol, and d...

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Abstract

The invention discloses a method for synthesizing oxiracetam intermediate 4-ethyl chloroacetoacetate and belongs to the field of pharmacy. The method is characterized in that chloroacetate and ethyl acetate react under the action of a catalyst to obtain the 4-ethyl chloroacetoacetate. The reaction process is: (1) evenly mixing the ethyl acetate, the catalyst and a solvent A, introducing protectivegas, controlling the pressure to be 0.3-0.5 Mpa, controlling the temperature to be 110-135 DEG C, adding a solution prepared from chloroacetate and a solvent B dropwise, controlling the addition timeto be 15-25 min, after chloroacetate and the solvent B are added, increasing the reaction temperature to 145-160 DEG C, increasing the pressure to 0.8-1 Mpa, continuing the reaction for 15-25 h, andthen ending the reaction; and (2) after a system is cooled, filtering the system to remove solid, adding filtrate to water with the volume being 3-5 times that of the filtrate, using a solvent C for extraction, and after an extract is dried with a drying agent, concentrating and evaporating the solvents to obtain a product. The method for synthesizing the oxiracetam intermediate 4-ethyl chloroacetoacetate has the advantages of relatively short steps, low process cost and few side effects.

Description

technical field [0001] The invention belongs to the field of pharmacy, in particular to a method for synthesizing oxiracetam intermediate 4-chloroacetoacetate ethyl. Background technique [0002] Oxiracetam (Oxiracetam) is pyrrolidone derivatives, chemical name is 4-hydroxyl-2-oxo-1-pyrrolidineacetamide, it can be used for the treatment of brain damage and the resulting neurological function loss, memory and intellectual impairment. Improve the memory and learning functions of patients with senile dementia and memory impairment; it can promote the synthesis of phosphorylcholine and phosphorylethanolamine, increase the ratio of ATP / ADP in the brain, and increase the synthesis of protein and nucleic acid in the brain. It is mainly used clinically. For the treatment of amnesia. [0003] Oxiracetam was first synthesized by the Italian ISF company in 1974. Over the years, although researchers have developed a variety of methods, it is still mainly synthesized using ethyl 4-chlo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/72C07C67/343B01J29/70
CPCC07C67/343B01J29/7003C07C69/72
Inventor 谭回李维平黄贤键刘文兰唐爱发李宗阳
Owner THE SECOND PEOPLES HOSPITAL OF SHENZHEN
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