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Preparation method of high activity myclobutanil

A high-activity, myclobutanil technology, applied in the preparation of carboxylic acid nitrile, the preparation of organic compounds, organic chemical methods, etc., can solve problems such as complex resolution, achieve high yield and purity, avoid cyano hydrolysis, composition improved effect

Active Publication Date: 2017-12-15
浙江大鹏药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although, as Chinese patent literature (publication number: CN106674139A) discloses a kind of preparation method of myclobutanil stereoisomer, the enantiomer of myclobutanil is resolved by adopting the method of simulated moving bed, although, its Highly active S-myclobutanil can be obtained through resolution, but it is only after the synthesis of the racemic mixture of myclobutanazole, followed by subsequent resolution, the resolution is too complicated
And at present, there is no report on the market that obtains a high content of highly active S-myclobutanil directly in the synthesis process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The high-activity solid base catalyst used in the following examples can be prepared according to the following method:

[0038] According to the ratio of each raw material in the high-activity solid catalyst, take 100g γ-Al 2 O 3 As a carrier, 2g aluminum sol was added as a binder, and 15g magnesium acetate (Mg(OAc) 2 ), after mixing and grinding for 1 hour, add 10 calcium hydroxide and 1g inorganic base. The inorganic base is an alkali metal hydroxide. The inorganic base can be sodium hydroxide or potassium hydroxide, and then 3g polyacrylamide is added as an auxiliary extrusion It is made by mixing and grinding for 2 hours, adding 20g of water, extruding into a strip, drying, and finally baking it in a muffle furnace at 500℃-600℃. In the examples, the calcination treatment was performed for 4 hours to obtain a composite solid base catalyst with high activity, which was ready for use.

Embodiment 2

[0040] The dimethyl sulfoxide solution of potassium triazole used in the following examples can be prepared according to the following method:

[0041] Add 80m of dimethyl sulfoxide and 25mg of toluene solvent into the reaction vessel, then add 125mg of triazole and 98mg of solid potassium hydroxide, heat, heat up to reflux and perform reflux dehydration reaction until the reaction is complete to obtain potassium triazole The water content of the potassium triazole dimethyl sulfoxide solution is less than or equal to 0.1%.

Embodiment 3

[0043] Add 300 mg of p-chlorobenzyl cyanide, 1500 mg of organic solvent toluene, 410 mg of n-butane bromide, and 30 mg of high-activity solid base catalyst into the three-necked flask of the reaction vessel. The temperature is increased, and the temperature is controlled to react at 30°C to 40°C for 2 hours. Then, the temperature was raised to 50°C±2°C and reacted for another three hours. After the reaction, the temperature was slowly lowered to room temperature, and then filtered to remove the solids. The filtrate was collected and subjected to vacuum distillation to remove the solvent to obtain Intermediate 2-( 4-chlorophenyl) capronitrile, the yield is 91%, and the content reaches more than 99%.

[0044] Then add 300mg of the intermediate 2-(4-chlorophenyl)capronitrile obtained above, 3mg of the chiral quaternary ammonium salt phase transfer catalyst cinchonidine and 250mg of dichloromethane to the three-necked flask of another reaction vessel. Dichloromethane can be used as b...

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Abstract

The invention relates to a preparation method of high activity myclobutanil, and belongs to the technical field of pesticide synthesis. In order to solve the existing problem of low activity of nitrile bacteria due to the difficulty of splitting, the preparation method of high activity myclobutanil is provided. The method includes the steps that compound 2 (4-chlorphenyl) hexanenitrile in formula I is added into a dichloromethane solvent under the action of chiral quaternary ammonium salt phase transfer catalyst, inorganic alkali water solution is added under the condition that the temperature is controlled to be 20 DEG C to 30 DEG C, the temperature is raised to 60 DEG C to 80 DEG C, after reaction, S-1-chlorine-2-nitrile base-2-(4-N-chlorophenyl) hexane is obtained; the chiral quaternary ammonium salt phase transfer catalyst is selected from cinchonidine and / or quinine, and the compound in formula II reacts with the dimethyl sulfoxide solution of anhydrous triazole potassium, and the high activity product-type compound in formula III S-type myclobutanil is obtained. The high acitivity reactive S-myclobutanil element in the product is significantly increased, the hydrolysis of cyanide is avoided, and the effects of higher yield and purity are achieved.

Description

Technical field [0001] The invention relates to a preparation method of high-activity myclobutanil and belongs to the technical field of pesticide synthesis. Background technique [0002] Myclobutanil is a class of triazole fungicides with protective and therapeutic activities. It mainly inhibits the biosynthesis of pathogenic ergosterol. It has the advantages of systemic, high efficiency and broad spectrum. It is excellent for preventing and treating various fungi. 的activity. [0003] For the synthesis process of myclobutanil, a three-step reaction is usually adopted at present: firstly, p-chlorobenzyl chloride, chloro-n-butane and tetrapropylammonium bromide (triethylamine) are used as raw materials, and 50% is added dropwise at a certain temperature. % Of liquid caustic soda to obtain 2-(4-chlorophenyl)capronitrile; then 2-(4-chlorophenyl)capronitrile, dichloromethane (dibromomethane), tetrapropylammonium bromide (triethylamine) ) Put into the reactor to obtain 1-chloro-2-nitri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07C255/35C07C253/30
CPCC07B2200/07C07C253/30C07D249/08C07C255/35
Inventor 徐学春徐大国杜青峰王辉王自田
Owner 浙江大鹏药业股份有限公司
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