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Synthesis method of fluopyram intermediate

A technology of fluopyram and its synthetic method, which is applied in the field of preparation of pesticide intermediates, can solve the problem of increased unit consumption of o-trifluoromethylbenzoyl chloride, high activity of o-trifluoromethylbenzoyl chloride, and poor stability of intermediate products and other issues, to achieve high product yield, reduce raw material costs, and facilitate post-processing effects

Active Publication Date: 2021-06-18
湖南速博生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method simplifies technological operation, but still will use noble metal catalyst palladium carbon to catalyze, and o-trifluoromethyl benzoyl chloride activity is very high, and side reaction easily occurs, uses alkali to make acid-binding agent simultaneously in addition, also It will react with o-trifluoromethylbenzoyl chloride, which will increase the unit consumption of relatively expensive o-trifluoromethylbenzoyl chloride, thereby increasing the cost
[0009] Patent WO2006067103A3 reports that o-trifluoromethylbenzoic acid is used as raw material to obtain N-acetoxymethyl-2-trifluoromethylbenzamide through acid chloride, amidation, hydroxymethylation and esterification, and then combined with 3-Chloro-5-trifluoromethyl-2-pyridinediethyl malonate is condensed to obtain the target product. Each step of this route is a classic reaction, and the reaction yield is high, but the intermediate product has poor stability and is not easy to purify. There are many by-products, and the reaction formula is as follows

Method used

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  • Synthesis method of fluopyram intermediate
  • Synthesis method of fluopyram intermediate
  • Synthesis method of fluopyram intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 47.0 g (1.00 mol) methanolamine was added to 6.6 g (0.10 mol) acetic acid, 0.9 g (2%) tetrabutylalonyl chloride, 140.0 g of 1,2-dichloroethane to add mechanical stirring, condensed tube, thermometer In the 1000 ml of three flasks, 112.3 g (1.10 mol) acetic anhydride was dripped over 30 minutes, and the reaction endpoint was determined according to liquid chromatography analysis. After the reaction was completed, the reaction was used to regulate the system pH. = 7, the water layer, the water wash the reaction liquid once, and the organic phase often pressed back to flow water to obtain an amino acetate 1,2-dichloroethane solution to carry out the next reaction.

[0030] 157.8 g (0.83 mol) was added to 2000 ml of three-port flasks with mechanical stirring, condensed tubes, and thermometer, and 108.6 g (0.91 mol) in 30 minutes. The sulfoxide, 80 to 85 ° C for 2 to 3 hours, determined according to the liquid chromatographic analysis results, after the reaction is completed, th...

Embodiment 2

[0034]47.0 g (1.00 mol) methanolamine was added to 7.8 g (0.13 mol) acetic acid, 2.2 g (5%) tetrabutylammonium chloride, 185.0 g 1, 2-dichloroethane to add a mechanical stirring, condensation, and thermometer. In a 1000 ml of three flasks, 122.5 g (1.2 mol) acetic anhydride was dripped over 30 minutes, and the reaction endpoint was determined according to liquid chromatography analysis. After the reaction was completed, the reaction was used to adjust the hydrogencarbonate aqueous solution to regulate the system pH. = 7, the water layer, the water wash the reaction liquid once, and the organic phase often pressed back to flow water to obtain an amino acetate 1,2-dichloroethane solution to carry out the next reaction.

[0035] 157.8 g (0.83 mol) was added to the 2000 ml of the three-port flask with mechanical stirring, condensed tubes, and thermometer, and 108.6 g (0.91 mol) was added to 30 minutes in 30 minutes. The sulfoxide, 80 to 85 ° C for 2 to 3 hours, determined according to...

Embodiment 3

[0039] 47.0 g (1.00 mol) methanolamine was added to 9.6 g (0.16 mol) acetic acid, 3.6 g (8%) tetrabutylammonium chloride, 230.0 g of 1,2-dichloroethane with mechanical stirring, condensed tube, thermometer In the 1000 ml of three flasks, 132.7 g (1.30 mol) acetic anhydride was added over 30 minutes, and the reaction endpoint was determined according to liquid chromatography analysis. After the reaction was completed, the hydrogencarbonate aqueous solution was used to regulate the system pH. = 7, the water layer, the water wash the reaction liquid once, and the organic phase often pressed back to flow water to obtain an amino acetate 1,2-dichloroethane solution to carry out the next reaction.

[0040] 157.8 g (0.83 mol) was added to 2000 ml of three-port flask with mechanical stirring, condensed tubes, and thermometer, 30 minutes (0.91 mol) in 30 minutes, 780 g 1,2-dichloroethane. Chloride, 80 to 85 ° C for 2 to 3 hours, determined according to the liquid chromatographic analysis r...

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Abstract

The invention discloses a synthesis method of a fluopyram intermediate, and belongs to the field of organic synthesis of pesticides. The process comprises the following steps: by taking methanol amine as a starting raw material, carrying out esterification reaction on methanol amine and acetic anhydride in the presence of acetic acid to obtain methyl aminoacetate, and carrying out amidation reaction on methyl aminoacetate and o-trifluoromethyl benzoyl chloride to obtain N-acetoxymethyl-2-trifluoromethyl benzamide; and finally, carrying out a splicing reaction with diethyl 3-chloro-5-trifluoromethyl-2-pyridylmalonate, so as to obtain the 3-chloro-5-trifluoromethyl-2-pyridylethyl (diethyl ester)-2-trifluoromethyl benzamide. The method adopts a convergent synthesis route, has the characteristics of low raw material cost, high atom economy, high yield, simple process operation and the like, and is suitable for large-scale production.

Description

Technical field [0001] The present invention relates to the technical field of preparation of pesticide intermediates, and more particularly to synthesis of 3-chloro-5-trifluoromethyl-2-pyridylethyl (diethyl ester) -2-trifluoromethylbenzamide. method. Background technique [0002] Fluopyram, its chemical name is N- (2- (3-chloro-5- (trifluoromethyl) -2-pyridyl) ethyl) -2-trifluoromethylbenzamide, It is a novel benzamide bactericide developed by Bayer Crop Science, inhibits mitochondrial breathing by hindering electron transfer of succinate dehydrogenase in the breathing chain. Fluoropylamide can inhibit spore germination, germination tube growth, mycelial growth, and spores. In the plant, fluoropyroformam is conductive and metastatic in the wood portion, mainly for controlling gray mold, white powder, late disease, frosty mildew, rice blast, etc. caused by fungal pathogens. Exhibits high activity and has broad application prospects. Molecular formula: C16H11CLF6N2O, the structura...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 刘鹏王宇杨湖平冯生维何阳
Owner 湖南速博生物技术有限公司
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