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Chemosynthesis method of 1-chloroformyl-4-ethyl-2, 3-dioxopiperazine

A technology of dioxopiperazine and chloroformyl, which is applied in the field of chemical synthesis of 1-chloroformyl-4-ethyl-2,3-dioxopiperazine, which can solve transportation and storage difficulties and potential safety hazards Large scale, difficult industrialization and other problems, to achieve the effect of high implementation value and social and economic benefits, safe and reliable production, and reasonable process conditions

Inactive Publication Date: 2005-09-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this process is that it uses phosgene, a highly toxic raw material that is restricted in the world, which has great potential safety hazards, and the reaction cycle is long, making industrialization difficult.
Harbin Pharmaceutical Second Factory Li Minghua et al. improved the reaction (see Heilongjiang Medicine, 1996, 9 (6): 327), using trichloromethyl chloroformate (diphosgene) to replace phosgene and N-ethyl-2, The reaction of 3-dioxopiperazine to prepare 1-chloroformyl-4-ethyl-2,3-dioxopiperazine has the disadvantage that the raw material diphosgene is a liquid with low content, difficulty in transportation and storage, and easily decomposed into phosgene
The above two synthetic methods have a large amount of three wastes and are difficult to handle

Method used

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  • Chemosynthesis method of 1-chloroformyl-4-ethyl-2, 3-dioxopiperazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] The molar ratio of feeding is N-ethyl-2,3-dioxopiperazine:bis(trichloromethyl)carbonate:pyridine=1:0.35:1

[0012] Add N-ethyl-2,3-dioxopiperazine, dichloromethane and pyridine into the reaction kettle, and after stirring evenly, add dichlorobis(trichloromethyl)carbonate dropwise at 5°C within 60 minutes. Methane solution, then react at 15°C for 10h, after the reaction is complete, filter to recover pyridine hydrochloride, concentrate the filtrate to recover the solvent, refine it with acetone, and dry it in vacuum. The yield is 86.8%, the melting point is 94.6-96.0°C, and the content (HPLC) is 99.1%.

Embodiment 2

[0014] The molar ratio of feeding is N-ethyl-2,3-dioxopiperazine:bis(trichloromethyl)carbonate:pyridine=1:0.55:1

[0015] Add N-ethyl-2,3-dioxopiperazine, dichloromethane and pyridine into the reaction kettle, and after stirring evenly, add dichlorobis(trichloromethyl)carbonate dropwise at 5°C within 60 minutes. Methane solution, then react at 10-15°C for 8 hours, after the reaction is complete, filter and recover pyridine hydrochloride, concentrate the filtrate to recover the solvent, refine it with acetone, and dry it in vacuum. The yield is 87.2%, the melting point is 95.2-96.0°C, and the content (HPLC) is 99.6 %.

Embodiment 3

[0017] The molar ratio of feeding is N-ethyl-2,3-dioxopiperazine:bis(trichloromethyl)carbonate:pyridine=1:0.8:1

[0018] Add N-ethyl-2,3-dioxopiperazine, dichloromethane and pyridine into the reaction kettle, and after stirring evenly, add dichlorobis(trichloromethyl)carbonate dropwise at 5°C within 60 minutes. Methane solution, then react at 15-20°C for 8 hours, after the reaction is complete, filter to recover pyridine hydrochloride, concentrate the filtrate to recover the solvent, refine it with acetone, and dry it in vacuum. The yield is 85.0%, the melting point is 94.0-96.1°C, and the content (HPLC) is 98.8%. .

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Abstract

A process for chemically synthesizing 1-chloroformacyl-4-ethyl-2,3-dioxypiperazine used to synthesize oxypiperazine penicillin and cefoperazone features the reaction between organic alkali as acid capturing agent, bis (trichloromethyl) carbonate and N-ethyl-2,3-dioxypiperazine. Its advantages are high output rate and basically no environmental pollution.

Description

technical field [0001] The present invention relates to a method of directly reacting N-ethyl-2,3-dioxopiperazine with bis(trichloromethyl)carbonate instead of phosgene to prepare 1-chloroformyl-4-ethyl-2,3 -The chemical synthesis method of dioxopiperazine, 1-chloroformyl-4-ethyl-2,3-dioxopiperazine is a kind of important pharmaceutical intermediate, mainly used in the synthesis of dioxopiperazine penicillin and cephalosporin Pererone, etc. Background technique [0002] Before the present invention was made, the chemical synthesis method of prior art 1-chloroformyl-4-ethyl-2,3-dioxopiperazine was based on phosgene or diphosgene and N-ethyl-2,3 -Dioxopiperazine is prepared by reacting raw materials. As proposed in PL 155058, N-ethyl-2,3-dioxopiperazine reacts with trimethylchlorosilane and triethylamine in tetrahydrofuran at 100-120°C for 10-20h, and then reacts with phosgene at room temperature. , The melting point of the product is 94-96°C. The disadvantage of this proc...

Claims

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Application Information

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IPC IPC(8): C07D241/08
Inventor 苏为科梁现蕊李永曙
Owner ZHEJIANG UNIV OF TECH
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