Synthesis method of picolinafen

A technology of difenachlor and a synthesis method, applied in the field of pharmaceutical synthesis, can solve the problems of long reaction route, harsh reaction conditions, difficult reaction, etc., achieves good scientific research value and industrial application potential, simplifies the reaction route, and facilitates the reaction conditions. effect

Inactive Publication Date: 2017-11-24
南通嘉禾化工有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, when route one condenses amides and 3-trifluoromethylphenol, because the amide steric hindrance is relatively large, the reaction is not easy to carry out, and the yield of the product is difficult to improve; route two has one more step of esterificatio

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A synthetic method for flumezachlor, comprising the following steps:

[0029] a) Add 23.1g (100mmol) 2-chloro-6-trichloromethylpyridine (formula II), 19.5g (120mmol) 3-trifluoromethylphenol (formula III), 4.8g (120mmol) into the reaction flask Sodium hydroxide, 100ml toluene and 200g DMSO, heating up, using Dean and Stark water separator to carry out azeotropic dehydration operation until no water comes out; distill off toluene, heat up to 150°C, keep warm for 8 hours, after the reaction DMSO was distilled off under reduced pressure; Water was added to dissolve inorganic salts, extracted with toluene, washed with water; Toluene was distilled off under reduced pressure to obtain 34g 2-(3-trifluoromethylphenoxy)-6-trichloromethylpyridine (formula IV ), the yield is 95%;

[0030] b) Add 34g (95mmol) 2-(3-trifluoromethylphenoxy)-6-trichloromethylpyridine (formula IV), 200ml 1,2 -Dichloroethane and 3.2g (20mmol) of anhydrous FeCl3, heated to reflux; then 1.7g (95mmol) of w...

Embodiment 2

[0033] A synthetic method for flumezachlor, comprising the following steps:

[0034] a) Add 23.1g (100mmol) 2-chloro-6-trichloromethylpyridine (formula II), 19.5g (120mmol) 3-trifluoromethylphenol (formula III), 4.8g (120mmol) into the reaction flask Sodium hydroxide, 100ml toluene and 200g DMSO, heating up, using Dean and Stark water separator to carry out azeotropic dehydration operation until no water comes out; distill off toluene, heat up to 150°C, keep warm for 8 hours, after the reaction DMSO was distilled off under reduced pressure; Water was added to dissolve inorganic salts, extracted with toluene, washed with water; Toluene was distilled off under reduced pressure to obtain 34g 2-(3-trifluoromethylphenoxy)-6-trichloromethylpyridine (formula IV ), the yield is 95%;

[0035] b) Add 34g (95mmol) 2-(3-trifluoromethylphenoxy)-6-trichloromethylpyridine (Formula IV) and 200ml concentrated hydrochloric acid into the reaction flask, heat up to 120°C, and keep it warm for 8 ...

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Abstract

The invention provides a synthesis method of picolinafen. The synthesis method comprises the following steps: reacting 2-chloro-6-trichloromethyl pyridine (formula II) with 3-trifluoromethyl phenol (formula III) to generate 2-(3-trifluoromethylphenoxyl)-6-trichloromethyl pyridine (formula IV); converting 2-(3-trifluoromethylphenoxyl)-6-trichloromethyl pyridine (formula IV) into 2-(3-trifluoromethylphenoxyl)-6-pyridine formyl chloride (formula V); and reacting 2-(3-trifluoromethylphenoxyl)-6-pyridine formyl chloride (formula V) with 4-fluoroaniline to generate picolinafen (formula I). By synthesizing a key intermediate namely 2-(3-trifluoromethylphenoxyl)-6-trichloromethyl pyridine (formula IV), the reaction route is well simplified, moreover, the reaction conditions can be reached easily, the product yield is high, and the synthesis method has a good value for scientific research and can be used in industry.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a method for synthesizing flumezachlor. Background technique [0002] Flufenachlor (Formula I) is an amide herbicide developed by BASF, which belongs to carotenoid biosynthesis inhibitors. Its common name is picolinafen, and its CAS accession number is [137641-05-5]. [0003] Document WO2007051759 reports two routes for the synthesis of flumezachlor (formula I). The first route is to use 2-chloro-6-trichloromethylpyridine as a raw material, first react with sulfuric acid to convert 2-chloro-6-pyridinecarbonyl chloride, the latter reacts with 4-fluoroaniline to form an amide, and finally the amide reacts with 3 - Condensation of trifluoromethylphenol to give flumezachlor (formula I): [0004] ; [0005] The second route is to esterify 2-chloro-6-pyridinecarbonyl chloride and alcohol into an ester, and then condense the latter with 3-trifluoromethylphenol to...

Claims

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Application Information

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IPC IPC(8): C07D213/81
CPCC07D213/81
Inventor 廖道华周耀明朱贲孝吴金明张曙光计敏磊
Owner 南通嘉禾化工有限公司
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