Synthetic method for orotic acid intermediate 5-alkoxy methylene hydantoin

A technology of alkoxymethylene hydantoin and synthesis method, which is applied in the field of synthesis of orotic acid intermediate 5-alkoxymethylene hydantoin, and can solve complex post-processing, pollution, and consumption of concentrated sulfuric acid Large volume and other problems, to achieve the effect of simple and economical treatment process, improved operating environment, and less three wastes

Inactive Publication Date: 2012-11-21
SHANGHAI HUAYI GRP CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by this invention is to provide a kind of synthetic method of orotic acid intermediate 5-alkoxymethylene hydantoin, to solve the excessive consumption of concentrated sulfuric acid in the existing clear acid production process, serious pollution, Technical defects such as complex post-processing

Method used

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  • Synthetic method for orotic acid intermediate 5-alkoxy methylene hydantoin
  • Synthetic method for orotic acid intermediate 5-alkoxy methylene hydantoin
  • Synthetic method for orotic acid intermediate 5-alkoxy methylene hydantoin

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Effect test

Embodiment 1

[0018] Get 200g 2-keto-dimethyl succinate and heat to dissolve in 1L xylene, then mix 113g urea, 20gSO 4 2- / ZrO 2 , put into 2L xylene, start heating and stirring, 2-keto-dimethyl succinate (R=CH 3 ) xylene solution is slowly dropped into the mixture of urea, solid super acid and xylene, the temperature of the oil bath is controlled at 130°C, and the reaction is carried out for 8-24 hours. When the reaction is finished, cool to room temperature, filter, and continue to use the filtered solid superacid, concentrate the mother liquor to obtain 5-methoxymethylenehydantoin, and the reaction yield is 72%. Washed twice with ethanol, directly used for the reaction of orotic acid in the next step.

Embodiment 2

[0020] Get 50g of 2-keto-dimethyl succinate and dissolve it in 200ml of toluene with heating, then add 28.3g of urea, 5gSO 4 2- / Fe 2 o 3 -Al 2 o 3 , put into 500ml toluene, start heating and stirring, 2-keto-dimethyl succinate (R=CH 3 ) toluene solution slowly drop into the mixture of urea, solid superacid and toluene, the oil bath temperature is controlled at 130°C, and the reaction is 8-24 hours. When the reaction is finished, cool to room temperature, filter, and continue to use the filtered solid superacid, concentrate the mother liquor to obtain 5-methoxymethylenehydantoin, and the reaction yield is 68%. Washed twice with ethanol, directly used for the reaction of orotic acid in the next step.

Embodiment 3

[0022] Get 84.9g urea, 15g solid super acid SO 4 2- / ZrO 2 -Al 2 o 3 , put into 1L xylene, and drop into 2-keto-diethyl succinate (R=C 2 h 5 ) 165g, start heating and stirring, in the mixture of xylene, the oil bath temperature is controlled at 130°C, react for 8-24 hours, when the reaction is over, cool to room temperature, filter, and continue to use the filtered solid superacid, concentrate the mother liquor , That is, 5-ethoxymethylene hydantoin was obtained, and the reaction yield was 74%. Washed twice with ethanol, directly used for the reaction of orotic acid in the next step.

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Abstract

The invention discloses a synthetic method for orotic acid intermediate 5-alkoxy methylene hydantoin. The method comprises the steps of using solid super acid as a catalyst; adding the solid super acid and urea to a benzene solvent; heating; dropping 2-keto-succinate to reaction liquid; agitating to react; and then filtering the solid super acid catalyst to be recycled after the reaction; distilling mother liquor to recover solvent which can be recycled, so as to obtain a raw product; and washing the crude product to obtain a target product. Compared with the prior art, the synthetic method disclosed by the invention has the advantages of simple and economical post-processing technology, less three wastes, and high yield, and is a novel method for synthesizing the 5-alkoxy methylene hydantoin.

Description

technical field [0001] The present invention relates to a kind of synthetic method of orotic acid intermediate 5-alkoxymethylene hydantoin, be specifically related to a kind of with the homologue of benzene as solvent, 2-keto-succinate and urea as raw material, A new method for the synthesis of 5-alkoxymethylenehydantoins under the catalysis of solid superacids. Background technique [0002] 5-Alkoxymethylene hydantoin (the structural formula is as follows A) is an important intermediate for the synthesis of orotic acid, which can be hydrolyzed and rearranged under alkaline conditions to obtain orotic acid (the structural formula is as follows shown in B). Orotic acid, also known as vitamin B13, usually contains a molecule of crystal water, is difficult to dissolve in water, and has poor solubility in most organic solvents. [0003] [0004] Orotic acid and its derivatives are widely used in medicine, mainly as liver medicine. In addition, in the cosmetics industry, or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/96
CPCY02P20/584
Inventor 代立张传好顾慧娟黄晓云廖本仁
Owner SHANGHAI HUAYI GRP CO
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