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A kind of preparation method of epoxiconazole intermediate and the preparation method of epoxiconazole

A technology of epoxiconazole and intermediates, which is applied in the preparation of epoxiconazole intermediates and the preparation of epoxiconazole, can solve the problems of high water and oxygen content requirements, safety and environmental protection problems, and unfavorable large-scale production. The effect of simple operation, high yield and easy availability of raw materials

Active Publication Date: 2019-03-15
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

US5268517 adopts the Grignard reagent method, which requires high moisture and oxygen content in the reaction process, has safety and environmental protection problems, and is not conducive to large-scale production. US20110295019 adopts the Horner-Wadsworth-Emmons reaction method, and the raw materials in this process are not easy to synthesize , and methyl nitrite is used in the raw material synthesis process, its vapor is very easy to form an explosive mixture with air, and a large amount of phosphorus-containing wastewater is produced during the HWE reaction process, causing great environmental pollution

Method used

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  • A kind of preparation method of epoxiconazole intermediate and the preparation method of epoxiconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Dissolve 25 grams of compound 1 in 50 mL of dimethyl sulfoxide, add 15 grams of sodium hydroxide and 1 gram of potassium iodide, heat up to 100 ° C, and react for 5 hours. When there is no compound 1 detected by GC, stop heating, cool to room temperature, and add acetic acid. The ethyl ester was washed with water, 5% sodium chloride solution and water in turn, separated, dried, and distilled under reduced pressure to remove ethyl acetate to obtain 21 g of compound 2, with a purity of >95% and a yield of 95.5%.

Embodiment 2

[0035] Dissolve 25 g of o-chlorobenzyl chloride in 50 mL of dimethyl sulfide, heat to 40 ° C, react at this temperature for 3 hours, stop heating, cool to 5 ° C, add 50 mL of toluene and 21 g of compound 2 obtained in Example 1 , then added potassium hydroxide in batches, heated to 80 ° C, collected the remaining dimethyl sulfide in the system, reacted for 2 hours, when GC could not detect compound 1, cooled to room temperature, added 50 mL of water, layered, and the organic layer was successively watered , washed with 5% sodium chloride solution and water, dried, and distilled under reduced pressure to obtain 40 g of compound 5 with a purity of >92% and a yield of 93%.

Embodiment 3

[0037] Dissolve 25 g of o-chlorobenzyl chloride in 50 mL of dimethyl sulfoxide, heat to 50 °C, react at this temperature for 3 hours, stop heating, cool to 5 °C, add 21 g of compound 2 obtained in Example 1, and then divide Sodium amide was added in batches, heated to 80°C, and reacted for 2 hours. When no compound 1 was detected by GC, it was cooled to room temperature, 50 mL of water was added, and the layers were separated. The organic layer was washed successively with water, 5% sodium chloride solution and water, and dried. Distillation under reduced pressure gave 35 g of compound 5 with a purity of >91% and a yield of 80%.

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Abstract

The invention relates to a preparation method of an epoxiconazole intermediate and a preparation method of epoxiconazole. The preparation method of the epoxiconazole intermediate comprises the following steps: taking O-chlorobenzyl chloride as a raw material and carrying out a reaction with dimethyl sulfide or dimethyl sulfoxide to obtain a compound 4, wherein the structural formula of the compound 4 is shown in the description; taking the compound 4 and a compound 2 as raw materials and carrying out a reaction under the action of alkali to obtain the epoxiconazole intermediate, wherein the structural formula of the compound 2 is shown in the description; the structural formula of the epoxiconazole intermediate is shown in the description. The preparation method of the epoxiconazole intermediate and the preparation method of epoxiconazole, provided by the invention, adopt a Corey epoxidation reaction method is used, have the advantages of being high in probability of raw material obtainment, simple to operate, good in stereoselectivity, high in yield, good in atom economy and the like, conform to the safety and environmental protection requirements and are suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of an epoxiconazole intermediate and a preparation method of epoxiconazole. Background technique [0002] Epoxiconazole, English common name: epoxiconazole, is a systemic selective fungicide. Its active ingredient, epoxiconazole, inhibits the synthesis of ergosterol in bacteria, hinders the formation of bacterial cell walls, and the molecule of epoxiconazole is effective against a fungal enzyme (14- dencthylase) has a strong affinity and can inhibit pathogenic fungi more effectively than currently known fungicides. Epoxiconazole can increase the chitinase activity of crops, cause the contraction of fungal haustoria, and inhibit the invasion of pathogens, which is a unique property of epoxiconazole among all triazole products. It has good control effect on leaf spot, powdery mildew, rust and anthracnose, white rot and other diseases on bananas, onions and garlic, celery, kidney beans, melons, asparagus, pea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D301/02C07D303/14C07D405/06
CPCC07D301/02C07D303/14C07D405/06
Inventor 姜宇华何永利陈佳刘玉超周志豪
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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