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Preparation method of pyrazole amide fungicide intermediate ketoxime compound

A technology of enone oxime and pyrazole amide, which is applied in the field of synthesis of chemical intermediates enone oxime compounds, to achieve mild reaction conditions, increase yield, and reduce toxicity

Active Publication Date: 2022-07-15
NANTONG JIANGSHAN AGROCHEM & CHEM LIMITED LIABILITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This invention is only a compounding technology of pesticides, and cannot be used for reference in the synthesis of pesticide intermediates

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Using ethyl acetate as solvent, 2-methyl-3-pent-2-oxycyclohex-2-enone (19.6 g, 0.1 mol) was added to the reaction flask, followed by anhydrous sodium acetate (9.1 g) , 0.11 mol), hydroxylamine hydrochloride (7.6 g, 0.11 mol) and a certain amount of process water. The whole system was heated to about 77°C, and the reaction was completed after 4 hours. After filtration, the sodium salt filter cake was washed with ethyl acetate, and the washing filtrate was mixed with the reaction solution for precipitation under the condition of -0.09MPa. When the temperature of the precipitation system reaches 110°C, the temperature is lowered to 50°C, the methanol of 5 times the weight of the oil in the three-necked flask is added, and the temperature is raised to reflux, and after reaching the reflux temperature, 4.5 times the weight of the oil is added with process water, cooled to room temperature, and filtered to obtain 15.6 Gram oxime, content 95.1%, yield 70.4%.

Embodiment 2

[0039] Using tetrahydrofuran as solvent, 2-methyl-3-pent-2-oxycyclohex-2-enone (19.6 g, 0.1 mol) was added to the reaction flask, followed by anhydrous sodium acetate (9.1 g, 0.11 mol) mol), hydroxylamine hydrochloride (7.6 g, 0.11 mol) and a certain amount of process water. The whole system was heated to about 70°C, and the reaction was completed after 4 hours. After filtration, the sodium salt filter cake was washed with tetrahydrofuran, and the washing filtrate was mixed with the reaction solution for precipitation under the condition of -0.09MPa. When the temperature of the precipitation system reaches 110°C, the temperature is lowered to 50°C, the methanol of 5 times the weight of the oil in the three-necked flask is added and the temperature is raised to reflux, after reaching the reflux temperature, process water 4.5 times the weight of the oil is added, cooled to room temperature, and filtered to obtain 15.9 Gram oxime, content 95.5%, yield 72.1%.

Embodiment 3

[0041] Using dioxane as solvent, 2-methyl-3-pent-2-oxycyclohex-2-enone (19.6 g, 0.1 mol) was added to the reaction flask, followed by adding anhydrous sodium propionate ( 10.5 g, 0.11 mol), hydroxylamine hydrochloride (7.6 g, 0.11 mol) and a certain amount of process water. The whole system was heated to about 80°C, and the reaction was completed after 4 hours of reflux. After filtration, the sodium salt filter cake was washed with dioxane, and the washing filtrate was mixed with the reaction solution for precipitation under the condition of -0.09MPa. When the temperature of the precipitation system reaches 110°C, the temperature is lowered to 50°C, the methanol of 5 times the weight of the oil in the three-necked flask is added, and the temperature is raised to reflux, and after reaching the reflux temperature, 4.5 times the weight of the oil is added with process water, cooled to room temperature, and filtered to obtain 15.6 Gram oxime, content 96.2%, yield 71.4%.

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Abstract

The invention relates to a preparation method of a pyrazole amide fungicide intermediate ketene oxime compound. The reaction is that the ketene ether compound, organic carboxylic acid sodium salt and hydroxylamine hydrochloride are oximeated in a solvent under the condition of 50° C. to the reflux temperature of the solvent, to obtain the ketene oxime compound. The appropriate solvent is preferably aqueous ethyl acetate, tetrahydrofuran or dioxane. The invention has mild reaction conditions, simple and convenient post-treatment, the product yield reaches about 70%, the purity reaches more than 95%, the content of by-product sodium chloride reaches 99%, and the economy and environmental protection are good.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing a chemical intermediate ketene oxime compound. Background technique [0002] Pyrazole amide compounds have certain bactericidal activity, CN104649973A announced that the pyrazole amide (general formula III) compound shown as the following reaction product has good bactericidal activity against rice sheath blight. The compound is obtained by the condensation reaction of the following ketene oxime compound (general formula II) and the following acid halide (general formula IV). The quality, content and yield of the ketene oxime compound determine the final product pyrazole amides Quality and cost of compounds. [0003] The conventional synthesis process of ketene oxime compounds uses raw material ketene ether compounds as raw materials and methanol as solvent, but ketene ether compounds (general formula I) have intracyclic double bonds, carbonyl groups an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/08C07C249/14C07C251/44
CPCC07C249/08C07C249/14C07C2601/16C07C251/44
Inventor 吴晓伟赵树林王徵王刚
Owner NANTONG JIANGSHAN AGROCHEM & CHEM LIMITED LIABILITY