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Preparation method of dimoxystrobin

A technology of kresastrobin and methoxyamine salt, which is applied in the field of pesticide chemistry, can solve the problems of many side reactions, high price, cumbersome operation, etc., and achieve the goal of reducing double grignard side reactions, eliminating side reactions, and easy access to raw materials Effect

Active Publication Date: 2021-02-26
XINFA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The above synthetic route 4 uses butyl nitrite for oximation, and the yield is low, resulting in low product content; the etherification reaction cycle is long; N-chlorosuccinimide is used, which is expensive and costly; and produces a large amount of waste water , difficult to handle, not environmentally friendly, not conducive to industrial amplification
[0020] In summary, the existing preparation technology of kresoximil has disadvantages such as many steps, cumbersome operation, large amount of three wastes, non-environmental protection, many side reactions, low product purity and yield, so the design of a simple, green and environmentally friendly The synthetic route of low cost, easy realization, less side reactions, high selectivity, high yield and high purity of kysoxastrobin is of great significance

Method used

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  • Preparation method of dimoxystrobin
  • Preparation method of dimoxystrobin
  • Preparation method of dimoxystrobin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1: 2-(2,5-dimethylphenoxymethyl) bromobenzene (Ⅲ 1 ) preparation

[0072] To a 1000 ml four-neck flask connected with stirring, a thermometer, a constant pressure dropping funnel and a reflux condenser, add 400 g of 1,2-dichloroethane, 82.8 g (0.6 mol) of potassium carbonate, 122.2 g (1.0 mol) ) 2,5-dimethylphenol, heated, kept between 40 and 45°C, added dropwise 215.8 grams (1.05 moles) of 2-chloromethylbromobenzene (Ⅱ 1 ), the dropwise addition was completed in about 3 hours, after which the reaction was stirred at 45 to 50°C for 2 hours, cooled to 20-25°C, filtered, the filter cake was washed with 1,2-dichloroethane, 100 grams each time, and the organic phases were combined, Distillation recovery solvent, vacuum distillation (150-175 ° C / 1-2mmHg) to obtain 275.7 grams of 2-(2,5-dimethylphenoxymethyl) bromobenzene (Ⅲ 1 ), yield 94.6%, gas phase purity 99.9%.

[0073] The NMR data of the resulting product are as follows:

[0074] 1 H NMR (400MHz, DMSO-d ...

Embodiment 2

[0075] Example 2: 2-(2,5-dimethylphenoxymethyl) bromobenzene (Ⅲ 1 ) preparation

[0076] To a 1000 ml four-necked flask connected with stirring, a thermometer, a constant pressure dropping funnel and a reflux condenser, add 500 g of dichloromethane, 82.8 g (0.6 mol) of potassium carbonate, 122.2 g (1.0 mol) of 2,5- Dimethylphenol, heated, kept between 30 and 35 ° C, added dropwise 262.5 grams (1.05 moles) of 2-bromomethyl bromobenzene (II 2 ), the dropwise addition was completed in about 3 hours, thereafter 35 to 40°C stirred and reacted for 2 hours, cooled to 20-25°C, filtered, the filter cake was washed with dichloromethane, 100 grams each time, the organic phases were combined, the solvent was recovered by distillation, and the Pressure distillation (150-175 ℃ / 1-2mmHg) obtains 273.8 grams of 2-(2,5-dimethylphenoxymethyl) bromobenzene (Ⅲ 1 ), yield 94.0%, gas phase purity 99.8%.

Embodiment 3

[0077] Example 3: Preparation of N-methyl-2-(2,5-dimethylphenoxymethyl)phenyloxalamide (Ⅴ)

[0078] Under nitrogen protection, 150 grams of tetrahydrofuran, 2.7 grams (0.11 moles) of magnesium powder, 0.5 grams of 1,2-dibromoethane, 1.5 grams of 2 prepared in Example 2 were added to a 500 milliliter four-necked flask equipped with a stirring and thermometer. -(2,5-Dimethylphenoxymethyl)bromobenzene(Ⅲ 1 ), 0.05 gram of iodine, and initiated Grignard reaction at 40-45°C for 0.2 hours; between 40-45°C, 27.6 grams (0.1 moles in total) of 2-(2,5-dimethylphenoxy) prepared in Example 1 were added dropwise Methyl)bromobenzene(Ⅲ 1 ) and 100 grams of tetrahydrofuran, drop it in 2 hours, then stir and react at 45-50°C under nitrogen for 3 hours, and cool to 20-25°C to obtain a reaction solution containing Grignard reagent; Transfer the liquid to a constant pressure dropping funnel, keep it between 20-25°C, and add it dropwise to a mixed solution of 17.6 grams (0.15 moles) of N-methyl o...

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Abstract

The invention provides a preparation method of dimoxystrobin. According to the method, 2-(2, 5-dimethylphenoxy methyl) halogenated benzene is prepared from 2-halogenated methyl halogenated benzene and2, 5-dimethylphenol through an etherification reaction, then the 2-(2, 5-dimethylphenoxy methyl) halogenated benzene and magnesium metal are subjected to a Grignard reaction to prepare a corresponding Grignard reagent, and obtained reaction liquid containing the Grignard reagent is dropwise added into Nmethyl oxalic acid monoester monoamide to prepare N-methyl-2-(2, 5-dimethylphenoxy methyl) halogenated benzene, and finally, a condensation reaction is carried out on the 2-(3, 5-dimethylphenoxy) phenyl oxamide and methoxylamine salt to prepare dimoxystrobin. The method has the advantages of cheap and accessible raw materials and low cost; the technological process is simple and short, and dimoxystrobin can be prepared only through three-step reaction; reaction conditions are easy to realize, operation is safe, simple and convenient, process wastewater yield is low, and environmental friendliness is achieved; raw materials and intermediate products are high in stability, high in reaction activity and selectivity and less in side reaction; and the obtained dimoxystrobin has the advantages of few impurities, high purity and high yield, and is beneficial to industrial production of dimoxystrobin.

Description

technical field [0001] The invention relates to a preparation method of kresastrobin, which belongs to the technical field of pesticide chemistry. Background technique [0002] Kresastrobin (I), the English name is Dimoxystrobin, the CAS number is 149961-52-4, the English name is (E)-2-(2,5-Dimethylphenoxymethyl)-α-methoxyimino-N-methylphenylacetamide, and its structural formula is as follows: [0003] [0004] Kysoxystrobin is a new type of methoxyacrylate systemic fungicide discovered by Shionogi Co., Ltd. of Japan and jointly developed with BASF. It is mainly compounded with triazole fungicide epoxiconazole. and eradicating activity, which can effectively prevent and control the main diseases of cereal crops and winter wheat; in 2014, the global sales reached 70 million US dollars, and it has broad development and application prospects. [0005] At present, the preparation method of kresastrobin in the prior art is as follows: [0006] Patent documents US8575366 and ...

Claims

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Application Information

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IPC IPC(8): C07C249/04C07C251/48C07C41/16C07C43/225C07C231/12C07C235/78
CPCC07C249/04C07C41/16C07C231/12C07C251/48C07C43/225C07C235/78
Inventor 戚聿新吕强三王海涛
Owner XINFA PHARMA
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