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Method for preparing 2,4-dichloro-10,11-dihydro-5H-dibenzo[a, d] cycloheptene-5-one

A technology of cycloheptene and dichlorophenylacetic acid, applied in the field of preparation of 2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, It can solve the problems of complex post-processing operation, low atom utilization rate, and low total yield, and achieve the effect of easy acquisition, high atom utilization rate, and simplified post-processing process

Active Publication Date: 2014-09-10
SUZHOU CHIEN SHIUNG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The above three methods have long routes, low total yield, complex post-treatment operations, and all have undergone Wittig reaction, resulting in a large amount of organic phosphorus waste and low atom utilization.

Method used

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  • Method for preparing 2,4-dichloro-10,11-dihydro-5H-dibenzo[a, d] cycloheptene-5-one
  • Method for preparing 2,4-dichloro-10,11-dihydro-5H-dibenzo[a, d] cycloheptene-5-one
  • Method for preparing 2,4-dichloro-10,11-dihydro-5H-dibenzo[a, d] cycloheptene-5-one

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1: Preparation of 2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

[0032] Use phthalic anhydride and 3,5-dichlorophenylacetic acid as raw materials in a material ratio of 0.5:1, react in the liquid of 1-hexadecyl-3-methylimidazolium bromide, 1 - The liquid dosage of hexadecyl-3-methylimidazolium bromide is 1% of phthalic anhydride, slowly heated to 50°C, reacted for 24 hours, released the reaction solution, added to ice water, added ethyl acetate Extraction and liquid separation, the organic layer was evaporated to remove the solvent under reduced pressure to obtain 3-(3,5-dichlorobenzylidene)isobenzofuran-1(3H)-one as a solid;

[0033] Add the solid 3-(3,5-dichlorobenzylidene)isobenzofuran-1(3H)-one to the ethanol solution, replace it with nitrogen for 3 times, add 10% palladium carbon to the mixture, and heat to 100 ℃, continue to flow hydrogen, react for 0.5 hours, and the reaction pressure is 1 atm. After the reaction is completed, filter out p...

Embodiment 2

[0035] Example 2: Preparation of 2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

[0036] Use phthalic anhydride and 3,5-dichlorophenylacetic acid as raw materials according to the material ratio of 1:1, react in the liquid of alkyl quaternary ammonium ions, and the liquid dosage of alkyl quaternary ammonium ions is o 5% of phthalic anhydride, slowly heated to 200 ° C, reacted for 0.5 hours, released the reaction solution, added to ice water, added ethyl acetate for extraction, liquid separation, and evaporated the solvent from the organic layer under reduced pressure to obtain 3-(3 , 5-dichlorobenzylidene) isobenzofuran-1(3H)-one solid;

[0037] Add the solid 3-(3,5-dichlorobenzylidene)isobenzofuran-1(3H)-one to the ethanol solution, replace it with nitrogen for 3 times, add 10% Raney nickel to the mixture, and heat to 200°C, continue to flow hydrogen, react for 10 hours, and the reaction pressure is 20atm. After the reaction, filter out Raney nickel, and distill...

Embodiment 3

[0039] Example 3: Preparation of 2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

[0040] With phthalic anhydride and 3,5-dichlorophenylacetic acid as raw material according to the material ratio of 2:1, react in the liquid of dialkyl imidazolium ion, the liquid consumption of dialkyl imidazolium ion is o 10% of phthalic anhydride, slowly heated to 100 ° C, reacted for 10 hours, released the reaction solution, added to ice water, added ethyl acetate for extraction, liquid separation, and evaporated the solvent from the organic layer under reduced pressure to obtain 3-(3 , 5-dichlorobenzylidene) isobenzofuran-1(3H)-one solid;

[0041] Add the solid 3-(3,5-dichlorobenzylidene)isobenzofuran-1(3H)-one to the ethanol solution, replace it with nitrogen for 3 times, add 10% palladium carbon to the mixture, and the reaction temperature is 0°C, continue to flow hydrogen, react for 48 hours, and the reaction pressure is 100atm. After the reaction, filter out palladium carbo...

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Abstract

The invention relates to a method for preparing 2,4-dichloro-10,11-dihydro-5H-dibenzo[a, d] cycloheptene-5-one. The method comprises the steps of reacting phthalic anhydride and 3,5-dichlorophenylacetic acid as starting materials in an ionic liquid system to generate 3-(3,5-dichlorobenzylidene)isobenzofuran-1(3H)-one, carrying out reduction reaction to obtain 2-(3,5-dichlorophenethyl)benzoic acid as an intermediate, and then carrying out cyclization to obtain 2,4-dichloro-10,11-dihydro-5H-dibenzo[a, d] cycloheptene-5-one. By virtue of the method, the synthetic route is greatly shortened, raw materials are cheap and easily available, the energy consumption and difficulty of the post-treatment are decreased and the emission of three wastes is reduced.

Description

technical field [0001] The present invention relates to a process for the preparation of 2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, in particular by forming the intermediate product 2-(3 , 5-dichlorophenethyl) benzoic acid is further cyclized to form 2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one. Background technique [0002] Antifungal infection drug Eboconazole nitrate chemical name is 1-(2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)imidazole nitrate , whose structure is shown in the following chemical structure formula, was developed by Spanish pharmaceutical company Chiesi, and then authorized Dr Reddys Laboratories to jointly develop. The drug is an imidazole antifungal drug, clinically used for skin fungal infection, and its mechanism of action is the same as other imidazole antifungal drugs. Its structure is as follows: [0003] [0004] 1-(2,4-Dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)imidazole nitrate....

Claims

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Application Information

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IPC IPC(8): C07C49/697C07C45/45
CPCC07C45/455C07C51/09C07C2603/32C07D307/88C07C49/697C07C63/70
Inventor 程炜汤俊梅贾红圣顾准王杨金浩
Owner SUZHOU CHIEN SHIUNG INST OF TECH