Method of synthesizing 1-methyl hydantoin

A synthesis method, the technology of methylhydantoin, applied in the field of synthesis of 1-methylhydantoin, can solve the problems of complicated synthetic routes and the use of highly toxic drugs, and achieve improved safety, reduced synthetic costs, and simple and easy synthetic routes line effect

Inactive Publication Date: 2010-06-23
王永生
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The invention provides a method for synthesizing 1-methylhydantoin to solve the problems of using highly toxic drugs and complex synthetic routes in the synthesis

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Add 46.5 g of 30% methylamine aqueous solution, 106 g of 10% sodium carbonate aqueous solution, and 87.5 g of 20% sodium chloroacetate aqueous solution into a 500 ml four-necked bottle, and react at 50° C. for 4 hours. Methylamine was distilled off and the pH was adjusted to 2. Heat to 100°C, add 91g of 8% sodium cyanate aqueous solution dropwise under reflux, stir and react for 30 minutes, add 7.3g of solid sodium cyanate to continue the reaction for 90 minutes, cool to 5°C, add 25g of 98% concentrated sulfuric acid , heated to 100° C. for reflux reaction for 2 hr, and evaporated to dryness under reduced pressure to obtain 9.85 g (59.4%) of crude product. The synthesized product is recrystallized and purified with chloroform, and the purity of the purified product can reach more than 99% through high performance liquid phase detection.

Embodiment 2

[0011] Add 46.5 g of 30% methylamine aqueous solution, 106 g of 10% sodium carbonate aqueous solution, and 87.5 g of 20% sodium chloroacetate aqueous solution into a 500 ml four-necked bottle, and react at 60° C. for 4 hours. Methylamine was distilled off and the pH was adjusted to 2. Heat to 100°C, add 91g of 8% sodium cyanate aqueous solution dropwise under reflux, stir and react for 30 minutes, add 7.3g of solid sodium cyanate to continue the reaction for 90 minutes, cool to 5°C, add 25g of 98% concentrated sulfuric acid , heated to 100° C., refluxed for 2 hr, and evaporated to dryness under reduced pressure to obtain 10.77 g (62.5%) of crude product. The synthesized product is recrystallized and purified with chloroform, and the purity of the purified product can reach more than 99% through high performance liquid phase detection.

Embodiment 3

[0013] Add 46.5 g of 30% methylamine aqueous solution, 106 g of 10% sodium carbonate aqueous solution, and 87.5 g of 20% sodium chloroacetate aqueous solution into a 500 ml four-necked bottle, and react at 70° C. for 4 hours. Methylamine was distilled off and the pH was adjusted to 2. Heat to 100°C, add 91g of 8% sodium cyanate aqueous solution dropwise under reflux, stir and react for 30 minutes, add 7.3g of solid sodium cyanate to continue the reaction for 90 minutes, cool to 5°C, add 25g of 98% concentrated sulfuric acid , heated to 100° C., refluxed for 2 hr, and evaporated to dryness under reduced pressure to obtain 10.18 g (61.4%) of crude product. The synthesized product is recrystallized and purified with chloroform, and the purity of the purified product can reach more than 99% through high performance liquid phase detection.

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Abstract

The present invention relates to a synthetic method of 1-methyl hydantoin, which belongs to synthetic method of compounds. The synthetic method includes following steps, adding 46.5g 30% aminomethane water solution, 106g 10% sodium carbonate water solution and 87.5g 20% 500ml 4-opening flasksodium monochloracetate water solution to react for 3 to 5hr at 50 to 70 DEG C; vaporizing to remove aminomethane and regulating pH value to 2; Heating to 100DEG C, dropping 91g 8% sodium cyanate water solution, agitating and reacting 30 minutes, adding 7.3g sodium cyanate solid to react 90 minutes, then cooling it to 5 DEG C, adding 25g concentrated sulfuric acid, heating to 100 DEG C and reflux reacting 2hr, generating crude product by vacuum distilling. The present invention is characterized in thatit implement green chemical because of avoiding using hypertoxic medicine of hydroxy acetonitrile and enhance the safety of operation, and its synthesis cost is low, entire syntheticroute is more simple, which is suitable for large scale industrial production.

Description

technical field [0001] The invention belongs to the synthesis method of compounds, in particular to the synthesis method of 1-methylhydantoin. Background technique [0002] 1-Methylhydantoin is a kind of hydantoin derivatives. It has a wide range of pharmacological effects, such as anti-inflammatory, anti-hypoproteinemia, elimination of active oxygen and free radicals, etc. The synthetic method literature report of 1-methylhydantoin is less, at present there are 1-benzyl-5-alkoxyhydantoin, 1-amino-2,4-hydantoin, 5-(substituted naphthyl) ethyl The synthetic routes of lactourea and other related compounds, in which the synthetic method of 1-benzyl-5-alkoxyhydantoin uses the highly toxic drug hydroxyacetonitrile, so it does not conform to green chemistry, and 1-amino-2,4-ethane The synthesis method of lactoins has a low yield. Contents of the invention [0003] The invention provides a method for synthesizing 1-methylhydantoin so as to solve the problems of using highly tox...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/72
Inventor 王永生李桂英白雪媛杨桠楠
Owner 王永生
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