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Method for synthesizing fluopyram

A technology for synthesizing fluopyram and fluopyram, applied in the fields of fine chemicals and organic synthesis, can solve problems such as pollution, and achieve the effects of high reaction yield, high product purity and short reaction route

Active Publication Date: 2021-09-24
陕西泰合利华工业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthetic step is shortened to 3 step reaction by the 5 step reaction in method one, but the o-trifluorobenzoic anhydride or o-trifluorobenzoic acid tert-butyl formic anhydride used in this method are not commercial reagents, need self-preparation, and synthetic method (ZhurnalOrganicheskoi Khimii, 1970,6,141) will produce a large amount of pyridine hydrochloride, causing serious pollution

Method used

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  • Method for synthesizing fluopyram
  • Method for synthesizing fluopyram
  • Method for synthesizing fluopyram

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1) Add 205g of 2-bromoethylamine hydrobromide, 10L of 2-methyltetrahydrofuran and 404g of triethylamine into a 5L reaction flask, stir at 27°C, react until the raw materials are completely converted, place the reaction in an ice-water bath, Add 208 g of o-trifluoromethylbenzoyl chloride containing 1.1 L of 2-methyltetrahydrofuran solution dropwise, and the dropwise addition is completed in about 30 minutes. Remove the ice-water bath and continue the reaction until the conversion of cyclopropylamine is complete. Add 1.1 L of water to the reaction solution. Stir for 15 minutes, separate the layers, concentrate the organic phase, replace the organic phase with 2.5 L of petroleum ether, and filter to obtain cyclopropylamine-1-yl (2-(trifluoromethyl)phenyl)methanone.

[0035] The amount of cyclopropylamine-1-yl(2-(trifluoromethyl)phenyl)methanone obtained was 196 g, and the yield was 91.1%.

[0036] The 1H NMR of the product obtained in this step and 13 The C NMR spectrum d...

Embodiment 2

[0041] 1) Add 20.5g of 2-bromoethylamine hydrobromide, 300mL of dichloromethane and 40.4g of triethylamine into a 1L reaction flask, stir at 27°C, react until the raw materials are completely converted, place the reaction in an ice-water bath, Add dropwise a solution containing 110mL of dichloromethane solution and 20.8g of o-trifluoromethylbenzoyl chloride, and the dropwise addition is completed in about 10 minutes. Remove the ice-water bath and continue the reaction until the conversion of cyclopropylamine is complete. Add 110mL of water to the reaction solution. Stir for 15 minutes, separate the liquids, concentrate the organic phase, replace the organic phase with 300 mL of petroleum ether, and filter to obtain 20 g of cyclopropylamine-1-yl (2-(trifluoromethyl)phenyl)methanone, with a yield of 92.6%.

[0042] 2) Add 20g of 2,3-dichloro-5-trifluoromethylpyridine and 200mL of tetrahydrofuran into a 10L reaction flask, stir until completely dissolved, place in a low-temperatur...

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Abstract

The invention provides a method for synthesizing fluopyram. The method comprises the following steps: taking commercially available 2-bromoethylamine hydrobromide as an initial raw material, carrying out self nucleophilic substitution reaction under an alkaline condition to prepare cyclopropylamine, and reacting the cyclopropylamine with o-trifluorobenzoyl chloride to obtain a key intermediate cyclopropylamine-1-yl (2-(trifluoromethyl) phenyl) ketone; and reacting 2,3-dichloro-5-trifluoromethylpyridine with the cyclopropylamine-1-yl (2-(trifluoromethyl) phenyl) ketone under the action of lithium alkylide to prepare the fluopyram. According to the method for synthesizing the fluopyram through the three-step reaction, the first-step reaction and the second-step reaction are one-pot reactions, the reaction yield is high, the synthesis process is simple, the product purity is high, and the method has huge application value.

Description

technical field [0001] The invention relates to the fields of organic synthesis and fine chemicals, in particular to a method for synthesizing fluopyram. Background technique [0002] Fluopyram (trade name: Lufida), its chemical name is N-[2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl]-2-trifluoromethyl Benzyl benzamide, cas: 658066-35-4, is a succinate dehydrogenase inhibitor fungicide developed by Bayer Crop Science, except for grapes, pears, bananas, apples, cucumbers, tomatoes and other vegetables and fields In addition to the prevention and control of spotted leaf spot, leaf spot, gray mold, powdery mildew, sclerotinia, early blight, etc. on crops, it is also a high-efficiency, green, and low-toxic nematicide for plant protection (WO2020020897 ). [0003] The synthetic method about fluopyridinamide in current literature mainly contains: [0004] Route 1: [0005] [0006] Patent documents WO2004016088 and WO2018114484 disclose that 2,3-dichloro-5-trifluoromethy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61
CPCC07D213/61Y02P20/55
Inventor 不公告发明人
Owner 陕西泰合利华工业有限公司
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