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Method for synthesizing non-steroidal antiphlogiston tiaprofenic acid

A non-steroidal anti-inflammatory drug and a synthesis method technology, applied in the direction of organic chemistry and the like, can solve problems such as pollution, and achieve the effects of simple process route, short circuit and avoiding pollution problems.

Inactive Publication Date: 2008-05-14
TIANJIN UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

[0013] The purpose of the present invention aims to overcome the deficiencies in the prior art, and provide a kind of synthetic method of non-steroidal anti-inflammatory drug tiaprofen acid, this synthetic method replaces rare, expensive and dangerous raw material with common cheap and safe raw material , the method of transition metal catalysis and ultrasonic catalysis avoids the problems of pollution and operation poisoning

Method used

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  • Method for synthesizing non-steroidal antiphlogiston tiaprofenic acid
  • Method for synthesizing non-steroidal antiphlogiston tiaprofenic acid
  • Method for synthesizing non-steroidal antiphlogiston tiaprofenic acid

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Embodiment 12

[0034] The preparation of embodiment 1.2-thiophene benzophenone:

[0035] In a three-necked flask equipped with mechanical stirring, a condenser and a thermometer, place anhydrous AlCl 3 10.0g, CS 2 30.0 g. Cool the suspension to 15-25°C, and dissolve thiophene 6.0g (71mmol) and benzoyl chloride 10.5g (75mmol) in 22.5g CS under stirring within 3.5h 2 The resulting solution was added to the flask through a condenser. The solution was allowed to warm to room temperature and stirring was continued for 3 more h, the mixture was left overnight. Then the mixture was refluxed on a water bath for 3.5h, cooled, poured on ice and extracted with 50mL ether. The extract was sequentially washed with 30mL saturated NaHCO 3 and 30mL of aqueous phase, and then in anhydrous CaCl 2 Dry on top. Ether was distilled off in a water bath, and the residue was distilled under reduced pressure to collect 11.7 g of 152-156°C / 8mmHg fraction with a yield of 87.3%. It solidified after cooling, with...

Embodiment 2

[0036] Example 2. Preparation of 2.5-benzoyl-α-methyl-2-thiophene malonate diethyl ester by ultrasonic method:

[0037] Add 0.94g (5mmol) of 2-thiophene benzophenone, 0.87g (5mmol) of diethyl methylmalonate, 0.82g (10mmol) of anhydrous NaOAc, Mn(OAc) to the reaction flask successively 3 4.56g (15mmol) and 30ml of acetic acid. Under the protection of nitrogen, it was heated to 80° C. under power ultrasonic radiation, and reacted for 5 h. After the solution was cooled to room temperature, 20 mL of ethyl acetate was added, and the precipitated solid was filtered. The filtrate was successively washed with 20ml of 10% NaHCO 3 solution, washed with 20mL saturated brine and washed with anhydrous MgSO 4 dry. The solvent was distilled off to obtain 1.65 g of light yellow oily liquid with a yield of 91.7%.

Embodiment 3

[0038] Example 3. Preparation of 5-benzoyl-α-methyl-2-thiophene malonate diethyl ester by non-ultrasonic method:

[0039] Add 1.88g of 2-thiophene benzophenone, 1.74g of diethyl methylmalonate, 1.60g of anhydrous NaOAc, Mn(OAc) to the reaction flask successively 310.56g and 50ml of acetic acid. Heated to 80°C and reacted for 16h. After the solution was cooled, 50 mL of benzene was added and filtered. The filtrate was sequentially washed with 10% NaHCO 3 solution, after washing with saturated brine, with anhydrous MgSO 4 dry. The solvent was evaporated and recrystallized to obtain 3.10 g of light yellow oily liquid with a yield of 86.14%.

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Abstract

The invention relates to tiaprofenic acid, that is, five-benzoyl-alpha-methyl-two-thiophene acetic acid, which is the ramification of the thiophene propionate and a new typed anti-inflaminatoroy and pain easing medicine. The invention is characterized in that two-thiophene benzophenone is obtained from the thiophene benzoylate by the benzene; the latter reacts with MDA-diethyl and generates the important intermediates five-benzoyl-alpha-methyl-two thiophene diethyl malonate under the action of the metal complex and the radiation of the power ultrasonic; the tiaprofenic acid is obtained after the saponification, acidization and decarboxylic reaction of the compound. The invention has the advantages of high yield up to seventy one percent calculated according to the thiophene, low cost of material, convenient and safe process, good product quality, and applicability to the industrial production.

Description

【Technical field】 [0001] The invention belongs to the production process of non-steroidal anti-inflammatory drugs, in particular to a synthesis method of non-steroidal anti-inflammatory drug tiaprofen acid. 【Background technique】 [0002] Tiaprofenic acid (tiaprofenic acid), also known as isothirone ibuprofen, phenylthiopropionic acid, chemically named as 5-benzoyl-α-methyl-2-thiopheneacetic acid, is produced by French Roussel-Excellence The non-steroidal anti-inflammatory analgesics of propionic acid acyl thienyl acetic acid derivatives developed by Roussol-Uclaf Central Research Institute, in 1984, Japan Roussol obtained a sales license under the trade name of Surgam. This product is a non-steroidal anti-inflammatory analgesic, which has antipyretic, analgesic and anti-inflammatory effects, can reduce swelling, relieve joint stiffness, relieve pain, and improve joint movement. It has been marketed in many countries. The mechanism of action is to inhibit the synthesis of p...

Claims

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Application Information

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IPC IPC(8): C07D333/24
Inventor 欧阳杰于龙江沈红芹陈宝泉于洁张有来
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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