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A kind of synthetic method of isoxaflutole

The technology of a kind of isoxaflutole and synthetic method is applied in the synthesis field of isoxaflutole, which can solve the problems of long production cycle, waste of production process materials and solvents, etc., and achieve low production cost, cheap material price and low by-product little effect

Active Publication Date: 2018-12-11
SHANGYU NUTRICHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to solve the problems of long production cycle and large waste of production process materials and solvents in the existing synthetic methods, the present invention provides a synthetic method of isoxaflutole with simple operation, short production cycle, and less use and emission of organic reagents

Method used

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  • A kind of synthetic method of isoxaflutole
  • A kind of synthetic method of isoxaflutole
  • A kind of synthetic method of isoxaflutole

Examples

Experimental program
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Effect test

Embodiment 1

[0093]Step (1): Methylthiolation reaction: Preparation of 2-methylthio-4-trifluoromethyl-benzonitrile:

[0094] Add 2-nitro-4-trifluoromethylbenzonitrile 320kg (1.47kmol) in reactor, toluene 1400kg, combined catalyst 5kg (sodium dodecylsulfonate and PEG400 each 2.5kg), open stirring and be warming up to 70 ℃, add dropwise 580kg (1.66kmol) of 20% sodium methyl mercaptide aqueous solution to the reaction kettle, the dropwise addition time is controlled at 3 hours, and the temperature of the control system is 70-80°C, after the dropwise addition is completed, the temperature is raised to reflux, and the insulation continues to react. The reaction process is controlled by HPLC, the content of 2-nitro-4-trifluoromethylbenzonitrile is less than 1%, the reaction time of heat preservation is 1 hour, the reaction is stopped, the layers are separated, and the organic layer is transferred to the precipitation kettle for desolvation under reduced pressure to obtain 320kg (1.42kmol) of 2-m...

Embodiment 2

[0107] Compared with Example 1, the difference is that in step (1), the molar ratio of 2-nitro-4-trifluoromethylbenzonitrile and sodium methylmercaptide is 1:1.5, and in the combined catalyst, dodecane The weight ratio of sodium sulfonate to PEG400 is 1:1.5. After the treatment, the yield of 2-methylthio-4-trifluoromethyl-benzonitrile is 98.1%, and the content is 97.1%.

[0108] The total yield of isoxaflutole was 81.3%, and the HPLC content was greater than 98.1%.

Embodiment 3

[0110] Compared with Example 1, the difference is that in step (1), the molar ratio of 2-nitro-4-trifluoromethylbenzonitrile and sodium methylmercaptide is 1:1.3, and in the combined catalyst, dodecane The weight ratio of sodium sulfonate to PEG400 is 1:0.5, and the reaction temperature is 50-60°C. After the treatment, the yield of 2-methylthio-4-trifluoromethyl-benzonitrile is 95.1%, and the content is 96.3 %.

[0111] The total yield of isoxaflutole is 73.6%, and the HPLC content is greater than 98.3%.

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Abstract

The invention discloses an isoxaflutole synthesizing method. According to the method, 2-nitro-4-trifluoromethylbenzonitrile serves as an initial raw material; and isoxaflutole is formed through methylthiolation, catalytic oxidation, condensation, hydrolysis, enolization and a ring-closure reaction. The synthesizing route provided in the method is reasonable; the conversion rate of each step is high; generated intermediates are high in purity; all the intermediates do not need further purification treatment; the process is simple; and the total yield of the isoxaflutole is greater than 73%, and HPLC purity is greater than 98%.

Description

technical field [0001] The invention belongs to the field of pesticide production, in particular to a method for synthesizing isoxaflutole. Background technique [0002] Isoxaflutole, the common name is Isoxaflutole, the chemical name is 5-cyclopropyl-4-(2-methanesulfonyl-4-trifluoromethyl)benzoylisoxazole, and its structural formula is shown in formula 1. [0003] [0004] Isoxaflutole is an organic heterocyclic selective systemic pre-emergence herbicide used for soil treatment in dry crop fields such as corn and sugarcane. It works mainly through absorption and conduction by weed young roots. It mainly controls various annual broad-leaved weeds such as velvetleum, quinoa, Kochia, pigskin, solanum nigrum, and amaranth. Poaceae weeds also have good control effect. [0005] The existing synthetic method of isoxaflutole is mostly with p-bromobenzotrifluoride and α-acetyl-γ-butyrolactone as starting raw materials, and after nitration, methylthiolation, oxidation and esteri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 冯应江温沛宏申宏伟陈佳易陈均坤吴凤华胡万全梅小玲孙久社徐金鹏梁俊芳陈国斌
Owner SHANGYU NUTRICHEM