Synthesis of 1,3-terahydro thiazolone compound

A technology of tetrahydrothiazolone and tetrahydrothiazolethione, applied in 1, can solve the problems of high price and difficult application of dioxane, and achieve the effect of large commercial application value, improvement of purity and quality, reduction of requirements and costs

Inactive Publication Date: 2003-03-19
CHENGDU KAOENSI SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the dioxane used in the reaction is expensive, the reaction process needs to be operated under pressure,

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0015] Toluene was used as the reaction solvent. 119 g of 1,3-tetrahydrothiazolthione-2 (II, R=H), 48 g of ethylene oxide and 500 ml of toluene were placed in a closed reactor and reacted at ~80°C for 6 hours. After the reaction was completed, the low boiling point was distilled off, filtered, and then the toluene was distilled off, and the residue was recrystallized with toluene to obtain 61 grams of a white crystal product, with a melting point of 52.5-54° C. and a compound (I) content (GC method) of 99.1% in the product .

example 2-5

[0017] Operation method is the same as example 1, and the reaction solvent adopts benzene, acetonitrile, dimethyl sulfoxide and butanone respectively, and the results are basically the same.

example 6

[0019] Ethanol was used as the reaction solvent. Add 119 g of 1,3-tetrahydrothiazolthione-2 (II, R=H) into 500 ml of ethanol, heat to 50°C to dissolve, and pass ethylene oxide gas at this temperature under stirring for about 2 hours. Add 48 grams of ethylene oxide. After the addition of ethylene oxide was complete, the reaction was heated to reflux under ethanol for 6 hours. After the reaction was completed, the solid was filtered off, the ethanol residue was removed under reduced pressure, and recrystallized with ethanol to obtain 67 grams of a white crystalline product with a melting point of 53-54° C. and a compound (I) content (GC method) of 99.5% in the product.

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Abstract

The present invention relates to the synthesis of 1,3-tetrahydro thiazolone-2 compounds as important intermediate for farm pesticide and some medicines. Compound 1,3-tetrahydro thiazothione-2 and epoxy ethane as materials are reacted. The solvent used in the reaction is at least one of water, C1-C4 fatty alcohol, C1-C4 fatty ketone, C1-C4 fatty ester, benzene, toluene, tetrahydrofuran, acetonitrile, dimethylformamide and dimethyl sulfoxide. The present invention has simple reaction condition, high product purity and high industrial application value. Through selecting and regulating solvent, epithioethane or polyglycol sulfide product may be obtained at the same time.

Description

technical field [0001] The invention relates to a synthetic method for preparing 1,3-tetrahydrothiazolone-2 compounds as important intermediates of pesticides and certain medicines. Background technique [0002] 1,3-Tetrahydrothiazolone-2 compounds (I) are important intermediates of some pesticides and medicines. With the difference of the initial raw materials used in the synthesis, the synthetic methods reported so far can include: [0003] The above synthetic methods have their own characteristics and problems respectively. For example, some require strict labor protection facilities because of the use of toxic gases such as phosgene; some use expensive raw materials such as aminoethanol, which makes the cost of the obtained target compound too high and difficult to achieve commercialization Production; some have too high requirements for reaction conditions, so that large-scale industrial production is limited; some have too many impurities in the synthetic product a...

Claims

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Application Information

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IPC IPC(8): C07D277/14
Inventor 郑彪杨启超李璐
Owner CHENGDU KAOENSI SCI & TECH
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