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Synthesis method of propyzamide based on oxidation reaction

A technology of propargyl and a synthesis method, which is applied in the field of organic chemical synthesis of pesticide molecules, can solve the problems of high toxicity, high safety risk, high cost of propargyl, and achieves low cost, mild reaction conditions, and high cost. The effect of commercial value and potential

Active Publication Date: 2021-09-17
深圳市谦陌通辰实验有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In view of the deficiencies of the prior art, in order to solve the problems of high cost, high safety risk and high toxicity in the synthesis of benzamide, the present invention provides a self-designed and innovative synthesis method

Method used

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  • Synthesis method of propyzamide based on oxidation reaction
  • Synthesis method of propyzamide based on oxidation reaction
  • Synthesis method of propyzamide based on oxidation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0015] According to one embodiment of the present invention, the synthesis method comprises the following steps:

[0016] S1.3,5-dichlorobenzoyl chloride is condensed with 2-amino-2 methyl 1-propanol in an organic solvent under the action of a coupling reagent to generate 3,5-dichloro-N-( 1-hydroxy-2-methylpropan-2-yl) benzamide;

[0017] S2. Use an oxidant to oxidize the 3,5-dichloro-N-(1-hydroxy-2-methylpropan-2-yl)benzamide obtained in step S1 in an organic solvent to generate 3,5-dichloro -N-(2-methyl-1-oxypropan-2-yl)benzamide;

[0018] S3. Using dimethyl (1-diazo-2-oxopropyl)phosphonate to 3,5-dichloro-N-(2-methyl-1-oxopropan-2-yl) obtained in step S2 Benzamide undergoes acetylenation reaction to generate 3,5-dichloro-N-(2-methylbut-3-yn-2-yl)benzamide, which is the product of benzamide.

[0019] In step S1, a condensation reaction is carried out in an organic solvent using a coupling reagent: the coupling reagent is N,N'-carbonyldiimidazole, dicyclohexylcarbodiimide,...

Embodiment 1

[0028]

[0029] Take an original bottom flask with a built-in stirring bar. Add 3,5-dichlorobenzoic acid (2.00 g, 10.47 mmol) and dichloromethane (20 ml) to it, stir, then add N,N'-dicarbonylimidazole (1.87 g, 11.52 mmol), stir For 30 minutes, react until the system dissolves. Add 2-amino-2-methyl-1-propanol (1.03 g, 11.52 mmol) into the reaction system and react at room temperature for 1 hour. After the reaction, water (40 ml) and dichloromethane (20 ml) were added to the reaction system, the organic phase (lower layer) was separated, and the aqueous phase was extracted three times with dichloromethane (10 ml). The organic phases were combined and concentrated to dryness to obtain the crude product of 3,5-dichloro-N-(1-hydroxy-2-methylpropan-2-yl)benzamide as light yellow oil with a yield of 89%, NMR The calculated content of the spectrum is 92%. The crude product was directly used in the next reaction.

Embodiment 2

[0031]

[0032] Take an original bottom flask with a built-in stirring bar. Add 3,5-dichloro-N-(1-hydroxy-2-methylpropan-2-yl)benzamide (2.05 g, 7.82 mmol) and dichloromethane (10 ml) to it, and stir until the system dissolves . Add Dess-Martin reagent (3.65 g, 8.60 mmol) and water (0.1 ml) to it, and react at room temperature for 1 hour. After the reaction was completed, a saturated sodium bicarbonate solution (5 ml) was added thereto and reacted for 5 minutes. The organic phase was separated, the aqueous phase was extracted three times with dichloromethane (5 ml), the combined organic phases were washed with saturated sodium thiosulfate solution (5 ml), and concentrated to dryness. 3,5-Dichloro-N-(2-methyl-1-oxypropan-2-yl)benzamide was obtained as a white solid with a yield of 95% and a purity of 95% calculated by NMR. This product was used directly in the next reaction.

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Abstract

The invention discloses a novel synthesis method of propyzamide. The method is characterized in that cheap dichlorobenzoic acid is used as a raw material. According to the method, the propyzamide product can be obtained without a complex reaction with harsh conditions and high toxicity and without using a high-activity, expensive and environment-harmful reagent. Compared with an existing synthesis method, the method has the advantage that high-activity acyl chloride reagents and expensive and easily degradable alkynyl amine substances are avoided. The method is integrally simple in route, economical, environment-friendly, safe and efficient, and has high industrial application potential.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis of pesticide molecules, and in particular relates to the preparation and industrialization of the pesticide molecule of benzamide, which is a self-designed and innovative synthesis method. Background technique [0002] Propyramide (also known as fenpyramide) is an amide herbicide. It is suitable for small seed leguminous crops, peanuts, soybeans, potatoes, lettuce and certain orchard cash crops. At present, herbicides in peanut fields are limited by crop safety, and often only a single herbicide with a limited bactericidal spectrum can be selected, and as a result, the production of weeds in peanut fields cannot be completely and effectively controlled. In addition, some herbicides are likely to cause residual toxicity to current crops or subsequent crops due to factors such as high water solubility, long field duration, large dosage, and uneven application. It has been found through re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C233/65C07C233/76C07C231/02C07C233/69
CPCC07C231/12C07C233/76C07C231/02C07C233/69C07C233/65
Inventor 颜春云程彦霓其他发明人请求不公开姓名
Owner 深圳市谦陌通辰实验有限公司
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