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Method for preparing 2-trifluoromethyl-10-oxaneones

A technology of trifluoromethyl and oxanone, applied in the field of synthesis of 2-trifluoromethyl-10-oxanone, which can solve the problems of high requirements for industrial equipment, danger of chlorine gas, high reaction cost, etc., and achieve simple operation Ease of operation, mild reaction conditions, and the effect of reducing production costs

Inactive Publication Date: 2003-10-08
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the use of chlorine gas has the problem of endangering safety, and the equipment is corroded, and the requirements for industrial equipment are high.
[0005] For the synthesis of intermediate diphenyl sulfide formic acid, except the method reported by the above-mentioned U.S. patent, German patent (DE3723079) has reported the synthetic method that takes o-chlorobenzoic acid and thiophenol as raw material, and the shortcoming of this method is to use lithium hydroxide As an acid-binding agent, tetrahydronaphthalene is used as a solvent, and the reaction cost is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 20g (0.13mol) of o-mercaptobenzoic acid, 12g (0.3mol) of sodium hydroxide, 120ml of DMF, 32g (0.177mol) of p-chlorobenzotrifluoride, heated to reflux, reacted for 20 hours, cooled to room temperature, poured into 300ml of water, added 1M hydrochloric acid, adjust PH=2-3, filter with suction, wash the filter cake with a small amount of water, and dry to obtain 34 g of solid, yield 87%, m.p.138-144°C.

[0015] 6g (0.02mol) of 2-(4-trifluoromethylphenylmercapto)benzoic acid, 20ml of concentrated sulfuric acid, heat up to reflux, react for 2 hours, cool to room temperature, slowly pour into 120ml of water, filter with suction, and dissolve the filter cake in 180ml of three Chloromethane, neutralized with dilute sodium hydroxide solution until it becomes alkaline, separated, the oil layer was washed with water until neutral, dried over anhydrous magnesium sulfate, distilled to remove chloroform, and the remaining solid was recrystallized with petroleum ether to obtain a light...

Embodiment 2

[0017] 20g (0.13mol) of o-mercaptobenzoic acid, 28g (0.5mol) of potassium hydroxide, 120ml of DMSO, 47.0g (0.26mol) of p-chlorobenzotrifluoride, heated to reflux, reacted for 24 hours, cooled to room temperature, poured into 300mL of water, Add 1M hydrochloric acid, adjust the pH to 2-3, filter with suction, wash the filter cake with a small amount of water, and dry to obtain 31.2 g of solid, yield 80.0%, m.p.136-144°C.

[0018] 6g (0.02mol) of 2-(4-trifluoromethylphenylmercapto)benzoic acid, 24mL of concentrated sulfuric acid, heated to reflux, reacted for 4 hours, cooled to room temperature, slowly added to 120ml of water, suction filtered, the filter cake was dispersed in 180ml of water, Neutralize with dilute sodium hydroxide solution until it becomes alkaline, filter, wash the filter cake with water, dry, and recrystallize with petroleum ether to obtain 2.6 g of light yellow solid, yield 46%, m.p.143-146°C.

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PUM

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Abstract

A process for preparing 2-trifluoromethyl-10-oxanone from p-trifluorotoluene and o-mercaptobenzoic acid includes nucleophilic substitution reaction on aryl ring to obtain diaryl thioether, and cyclization reaction with concentrated sulfuric acid. Its advantage is short period.

Description

technical field [0001] The present invention relates to the synthetic method of 2-trifluoromethyl-10-oxanone technical background [0002] 2-Trifluoromethyl-10-oxanone is an important pharmaceutical intermediate and an important intermediate for preparing the antidepressant trifluorothixene. Its structural formula is as follows: [0003] U.S. Patent (US925539) has reported the method of preparing 2-trifluoromethyl-10-oxanone through multi-step reaction with p-chlorobenzotrifluoride and o-mercaptobenzoic acid as raw materials: after p-chlorobenzotrifluoride is nitrated with mixed acid , to generate 3-nitro-4-chlorobenzotrifluoride, which reacts with o-mercaptobenzoic acid to generate 2-(4-trifluoromethyl-2-nitro)phenylmercaptobenzoic acid, which is then reduced by stannous chloride into the corresponding amine, the amine after diazotization deamination reaction to obtain intermediate 2-(4-trifluoromethyl) phenylmercaptobenzoic acid, the compound is cyclized by sulfuric aci...

Claims

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Application Information

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IPC IPC(8): C07D335/16
Inventor 吴范宏杨雪艳
Owner EAST CHINA UNIV OF SCI & TECH
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