Preparation method of cyproconazole key intermediate 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone

A technology of cyproconazole and chlorophenyl, which is applied in the field of preparation of the key intermediate 1--2-cyclopropyl-1-propanone of cyproconazole, can solve the problem of high cost, low total yield, Three wastes and other issues

Inactive Publication Date: 2012-09-19
JIANGXI HUASHI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] This route has a total of four steps of reaction, and a large amount of expensive solvents, boron trifluoride ether, sodium borohydride and other reagents are used. The cost is also high, and a large amount of three wastes are generated in the production process, and the total yield is low, and the product quality is poor. , currently does not have the advantage of competing with foreign companies

Method used

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  • Preparation method of cyproconazole key intermediate 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone
  • Preparation method of cyproconazole key intermediate 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone
  • Preparation method of cyproconazole key intermediate 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone

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Experimental program
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Effect test

Embodiment 1

[0025] Synthesis of compound (II):

[0026] Add 44 grams of 2-(4-chlorophenyl)-3-cyclopropyl-2-butenenitrile into a 1000 ml autoclave, then add 200 grams of methanol, 1.5 grams of 5% palladium-carbon alloy, and use Replace the air with nitrogen three times, and replace it with hydrogen twice to maintain a hydrogen pressure of 1.2MPa, then slowly heat to 60 degrees and react for about 8 hours, take a sample and analyze the reaction is complete, cool, release the pressure, filter and recover the catalyst after the material is released, and the filtrate is first normal pressure The methanol was recovered by distillation, and the methanol was thoroughly distilled under reduced pressure to obtain about 41.9 grams of a viscous substance with a purity of about 95% by GC analysis. Purified to obtain 42.0 g with a molar yield of 95.4%. In actual production, no further purification is required, and it is directly used in the next reaction.

Embodiment 2

[0028] Synthesis of compound (I);

[0029] Add 22 grams of compound (II) to 66 grams of dry DMSO, then add 22 grams of potassium hydroxide powder, stir evenly, and slowly and uniformly introduce oxygen flow. At this time, the reaction will exotherm, and the internal temperature will be kept at about 40 degrees. Introduce oxygen for about 16 hours, take a sample and analyze the reaction is complete, cool to 20 degrees, add 200 ml of water to dilute the reaction solution, then neutralize it with 10% dilute hydrochloric acid, extract twice with 100 ml of toluene, and combine the extracted The toluene liquid was washed once with water, and the toluene was recovered by atmospheric distillation first, and then the toluene was thoroughly distilled under negative pressure, and the obtained crude product was distilled by high vacuum with an oil pump, and about 17.5 grams of 95% (GC, area normalization method) purity of 1 -(4-Chlorophenyl)-2-cyclopropyl-1-acetonate (I), pale yellow liqu...

Embodiment 3

[0031] Synthesis of compound (II):

[0032] Add 44 grams of 2-(4-chlorophenyl)-3-cyclopropyl-2-butenenitrile into a 1000 ml autoclave, then add 200 grams of methanol, 1.5 grams of 5% palladium-carbon alloy, and use Replace the air with nitrogen three times, and replace it with hydrogen twice to maintain a hydrogen pressure of 1.2MPa, then slowly heat to 60 degrees and react for about 8 hours, take a sample and analyze the reaction is complete, cool, release the pressure, filter and recover the catalyst after the material is released, and the filtrate is first normal pressure The methanol was recovered by distillation, and the methanol was thoroughly distilled under reduced pressure to obtain about 42.4 grams of a viscous substance with a purity of about 95% by GC analysis. Purified to obtain 41.8 g with a molar yield of 95.0%. In actual production, no further purification is required, and it is directly used in the next reaction.

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Abstract

The invention relates to a preparation method of cyproconazole key intermediate 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone, comprising the following steps of: obtaining a compound (II) by 2-(4-chlorphenyl)-3-cyclopropyl-2-crotononitrile through selectively reducing double bonds; using the oxygen to oxidize cyan group in the compound (II) to carboxyl in the present of the catalyst, obtaining 80% of crude1-(4-chlorphenyl)-2-cyclopropyl-1-acetone; and finally, obtaining more than 95% of cyproconazole key intermediate 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone by high vacuum rectification. The method has the characteristics of high yield, good quality, low cost and safety in production, and can achieve industrial production completely.

Description

technical field [0001] The present invention relates to the preparation method of cyproconazole key intermediate 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone, [0002] A facile synthesis of the key intermediate cyproconazole 1-(4-chlorophenyl)-2-cyclopropyl-1- via 2-(4-chlorophenyl)-3-cyclopropyl-2-butenenitrile acetone. Background technique [0003] Cyproconazole is a high-efficiency and low-toxic triazole fungicide successfully developed by Sandoz AG. It was first launched in France in 1989 as a fungicide for barley foliage spraying, and later as a seed treatment agent, widely used in Europe and seed treatments for a variety of crops in the Americas. The bactericide has a wide bactericidal spectrum and less residue, is a sterol demethylation inhibitor, and has preventive and therapeutic effects. Against powdery mildews, rusts, spp. , Septoria spp., Septoria spp., and Scutellaria spp. are all effective. Mixed with other fungicides, it can well control cereal eye spot ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/813C07C45/32
CPCY02P20/584
Inventor 陶建华龚义斌夏颖
Owner JIANGXI HUASHI PHARMA
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