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Synthetic method of important intermediate of hexythiazox

A synthesis method and intermediate technology are applied in the field of preparation of important intermediates of pesticide technical materials, which can solve the problems of high price and low yield of raw and auxiliary materials, and achieve the effects of low cost, high yield and high content.

Active Publication Date: 2020-11-24
JIANGSU HEBEN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This route involves oximation and rearrangement reactions, the use of raw and auxiliary materials is relatively expensive, and the yield is relatively low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Put 91.0g of 98.9% lactic acid into the reaction kettle, without stirring at this time, first raise the temperature to 53-55°C, after the lactic acid melts, stir slowly, add 150.0g of thionyl chloride dropwise, and finish the reaction After 2-3 hours, excess thionyl chloride was removed to obtain intermediate I;

[0030] 2) Put 113.0g of chlorobenzene, 150.0g of anhydrous aluminum trichloride and 300.0g of dichloromethane into the reaction kettle, cool down to 10-30°C, drop all the intermediates I prepared above and react for 5-8h, Add 200 g of ice water to quench the reaction, separate the phases, and evaporate dichloromethane to dryness to obtain intermediate II;

[0031] 3) Put intermediate II, 55g of ammonium chloride, 3g of catalyst and 250g of dimethyl sulfoxide into the pressurized reactor, raise the temperature to 110-150°C, keep it warm for 5-8h, and cool down to 10- Evaporate dimethyl sulfoxide to dryness at 30°C to obtain the crude product of 2-amino-1-(p...

Embodiment 2

[0034] 1) Put 91.00g of 98.9% lactic acid into the reaction kettle, do not stir at this time, first raise the temperature to 53-55°C, after the lactic acid melts, stir slowly, add 142.80g of thionyl chloride dropwise, and finish the reaction 2 -3 hours, remove excess thionyl chloride to obtain intermediate I;

[0035] 2) Put 112.50g of chlorobenzene, 146.85g of anhydrous aluminum trichloride and 225.00g of dichloromethane into the reaction kettle, cool down to 10-30°C, drop all the intermediates I prepared above and react for 5-8h, Add 168.75 g of ice water to quench the reaction, separate the phases, and evaporate dichloromethane to dryness to obtain intermediate II;

[0036] 3) Put intermediate II, 53.50g of ammonium chloride, 0.92g of catalyst and 239.85g of dimethyl sulfoxide into the pressurized reactor, raise the temperature to 110-150°C, keep it warm for 5-8h, and cool down after passing the central control To 10-30°C, evaporate dimethyl sulfoxide to dryness to obtain ...

Embodiment 3

[0039] 1) Put 91.00g of 98.9% lactic acid into the reaction kettle, without stirring for now, first raise the temperature to 53-55°C, after the lactic acid melts, stir slowly, add 178.50g of thionyl chloride dropwise, and finish the reaction 2 -3 hours, remove excess thionyl chloride to obtain intermediate I;

[0040] 2) Put 123.75g of chlorobenzene, 160.20g of anhydrous aluminum trichloride and 495.00g of dichloromethane into the reaction kettle, cool down to 10-30°C, drop all the intermediates I prepared above and react for 5-8h, Add 371.25 g of ice water to quench the reaction, separate the phases, evaporate dichloromethane to dryness, and obtain intermediate II;

[0041] 3) Put intermediate II, 58.85g of ammonium chloride, 9.23g of catalyst and 479.70g of dimethyl sulfoxide into the pressurized reactor, raise the temperature to 110-150°C, keep it warm for 5-8h, and cool down after passing the central control To 10-30°C, evaporate dimethyl sulfoxide to dryness to obtain th...

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PUM

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Abstract

The invention discloses a synthetic method of an important intermediate of hexythiazox. The synthetic route comprises acyl chlorination reaction, Friedel-Crafts acylation reaction, amination reactionand refining process. The method of the invention has the advantages of low cost, high content and high yield; and according to the present invention, lactic acid is utilized through acyl chlorination, Friedel-Crafts acylation and amination to prepare 2-amino-1-(p-chlorophenyl) acetone hydrochloride, lactic acid is cheap and easy to obtain as a reaction raw material, and during the preparation process, the crude product of 2-amino-1-(p-chlorophenyl) acetone hydrochloride is purified by alkaline hydrolysis and acidification, with high content and high final yield.

Description

technical field [0001] The present invention relates to the field of preparation of important intermediates of pesticide technical materials, and specifically relates to a method for synthesizing important intermediates of hexythiazox. Background technique [0002] Hexythiazox has a wide spectrum of insecticidal properties, and is mainly contact-killing. It has a strong killing effect on the nymphs and eggs of various spider mites; it has low toxicity to humans and animals. It has very little impact on the class, and can be mixed with various pesticides such as lime sulfur mixture and Bordeaux mixture. [0003] At present, the preparation of hexythiazox mainly starts from its important intermediate 2-amino-1-(p-chlorophenyl)acetone hydrochloride, and through a series of reactions, hexythiazox is obtained; but 2-amino-1-( There are not many preparation methods of p-chlorophenyl) acetone hydrochloride, and the main route is: [0004] . [0005] This route involves oximati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/60C07C59/01C07C45/46C07C49/82C07C221/00C07C225/16
CPCC07C51/60C07C45/455C07C45/46C07C221/00C07C59/01C07C49/82C07C225/16
Inventor 冯魏陈华邓桂元贾利华李祥邢燕
Owner JIANGSU HEBEN BIOCHEM
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