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Method for preparing Celecoxib dione intermediate

A technology for celecoxib and intermediates, which is applied in the field of synthesis of small molecular compounds, and can solve the problems of difficulty in obtaining ultra-fine-grained carbonates and large dosages, etc.

Inactive Publication Date: 2019-11-05
HUNAN FANGSHENG PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, ultra-fine carbonates are difficult to obtain, and due to the large amount of use, a large amount of solid waste will be generated, which has caused huge environmental protection pressure for industrial production.

Method used

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  • Method for preparing Celecoxib dione intermediate
  • Method for preparing Celecoxib dione intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 1000ml reaction flask, add 500.0g toluene, 187.9g (1.40mol) p-methylacetophenone, 94.1g sodium methoxide (1.68mol), slowly add 238.8g ethyl trifluoroacetate (1.54mol) dropwise, Keep warm at 20-30°C, continue to react for 5 hours after the dropwise addition, adjust the pH value to 2 with the prepared 5N hydrochloric acid solution, and then wash twice with 500g purified water; the organic phase after washing is slowly cooled to -10°C~- Crystallize at 5°C for 2 hours, filter and dry to obtain 305.5 g of a light yellow solid with a molar yield of 94.8% and a purity of 99.8%.

Embodiment 2

[0022] In a 1000ml reaction flask, add 500.0g toluene, 187.9g (1.40mol) p-methyl acetophenone, 94.1g sodium methoxide (1.68), slowly add 238.8g ethyl trifluoroacetate (1.68mol) dropwise, keep warm 20~30℃, continue to react for 5h after the dropwise addition, adjust the pH value to 2 with the prepared 5N hydrochloric acid solution, and then wash twice with 500g purified water; the organic phase after washing is slowly cooled to -10℃0~- Crystallize at 5°C for 2 hours, filter and dry to obtain 307.1 g of a light yellow solid with a molar yield of 94.8% and a purity of 99.3%.

[0023] The present embodiment adopts different mol ratios, compares with embodiment 1, and its yield improves slightly, but product purity descends slightly.

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Abstract

The invention provides a method for preparing a Celecoxib dione intermediate. The method comprises the steps: subjecting p-methylacetophenone and ethyl trifluoroacetate to a reaction in the presence of sodium methylate, wherein toluene serves as a solvent, and a reaction temperature is 20 DEG C to 40 DEG C; carrying out quenching with a hydrochloric solution after the reaction is complete, then, carrying out washing with purified water, and carrying out standing to separate out an aqueous phase; and subjecting an organic phase to cooling crystallization, thereby obtaining a yellowish solid product. According to the method provided by the invention, the safety of industrial production of the Celecoxib dione intermediate can be improved, the process is very convenient, and meanwhile, the purity and yield of the product are not lowered.

Description

technical field [0001] The present invention relates to the synthetic field of small molecule compound, be specifically related to a kind of synthetic method of medicine and its intermediate. Background technique [0002] Celecoxib, the chemical name is 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (see the following formula I for its structural formula ), is a specific type 2 cyclooxygenase (COX-2) inhibitor, its selectivity to COX-2 is 375 times that of COX-1, and it is mainly used for the treatment of osteoarthritis and rheumatoid arthritis , has high anti-inflammatory activity, and almost no gastrointestinal side effects. [0003] [0004] The synthetic route of celecoxib is relatively simple, and it can be obtained through two-step synthesis. First, p-methylacetophenone undergoes Claisen condensation to obtain a β-diketone intermediate, and the latter is combined with p-hydrazinobenzenesulfonamide ring Synthetic celecoxib. [0005] C...

Claims

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Application Information

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IPC IPC(8): C07C49/80C07C45/72C07C45/81
CPCC07C45/72C07C45/81C07C49/80
Inventor 张庆华陈波阎智勇
Owner HUNAN FANGSHENG PHARMACEUTICAL CO LTD
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