Improved method for preparing aceclofenac

A technology of aceclofenac and diclofenac sodium, which is applied to the preparation of cyanide reaction, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of easy falling off of protective groups, acidolysis selectivity, low yield, etc., to avoid Effects of side reactions, improvement of product yield and purity, and improvement of reaction yield

Active Publication Date: 2009-09-16
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the above defects in the prior art, due to the fact that the protective group is easy to fall off and the poor selectivity of acidolysis causes side reactions during the condensation process, resulting in the problem that the yield is generally low. The introduction of a suitable catalyst improves the speed of the

Method used

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  • Improved method for preparing aceclofenac

Examples

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Effect test

Embodiment 1

[0035] Example 1 Preparation of tert-butyl 2-(2,6-dichloroanilino)phenylacetoxyacetate (compound III)

[0036] Put 20 g of diclofenac sodium, 0.5 g of sodium iodide, 10.4 g of tert-butyl chloroacetate, and 100 ml of acetone into the reaction flask, heat to about 60° C. for reflux reaction for 2 hours, and spot the plate with TLC (developing agent: n-hexane: ethyl acetate = 6:1 (volume ratio)) After the reaction, filter out sodium chloride, recover acetone at 60-65°C under normal pressure, then evaporate the acetone to dryness under reduced pressure, add methanol to reflux to refine the intermediate, cool and crystallize, filter, and vacuum dry Oven drying (temperature 45°C-55°C, vacuum degree ≥ 0.09 MPa) yielded 25.0 g of white crystals (yield: 97.0%, mp: 87.8-88.2°C).

Embodiment 2

[0037] Example 2 Preparation of tert-butyl 2-(2,6-dichloroanilino)phenylacetoxyacetate (compound III)

[0038]Put 20 g of diclofenac sodium, 0.6 g of potassium iodide, 11.3 g of tert-butyl chloroacetate, and 200 ml of acetone into the reaction bottle, heat it to about 60° C. for reflux reaction for 2.5 hours, and spot the plate with TLC (developing agent: n-hexane: ethyl acetate=6: 1 (volume ratio)) After the reaction, remove sodium chloride by filtration, recover acetone under normal pressure at 60-65°C, then evaporate acetone to dryness under reduced pressure, add methanol to reflux to refine the intermediate, cool and crystallize, filter, and dry in a vacuum oven (45°C-55°C, vacuum degree ≥0.09 MPa), 24.3 g of white crystals were obtained (yield: 94.2%, mp: 87.6-88.2°C).

Embodiment 3

[0039] Example 3 Preparation of tert-butyl 2-(2,6-dichloroanilino)phenylacetoxyacetate (compound III)

[0040] Put 20 g of diclofenac sodium, 0.5 g of sodium iodide, 10.4 g of tert-butyl chloroacetate, and 80 ml of DMF into the reaction bottle, heat it to about 80 ° C for 1.5 hours, and spot the plate with TLC (developing agent: n-hexane: ethyl acetate = 6: 1 (volume ratio)) After the reaction, filter out sodium chloride, evaporate DMF under reduced pressure, add methanol to reflux to refine the intermediate, cool and crystallize, filter, and dry in a vacuum oven (45 ° C ~ 55 ° C, vacuum degree ≥ 0.09MPa), to obtain 24.8g of white crystals (yield: 96.2%, mp: 87.3-87.7°C).

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Abstract

The invention provides an improved method used for preparing aceclofenac. The improved method is characterized in that (1) the method takes diclofenac sodium and tert-butyl chloroacetate as raw materials and iodide as a catalyst, and heats the substances to carry out condensation reaction; (2) the method takes tert-butyl aceclofenac as a raw material to carry out acidolysis reaction under the action of phenol and acid, and obtains aceclofenac crystal after post treatment and fine purification; and the total yield of both steps is above 88 percent and the content is over 99.2 percent (detected by HPLC). The improved method increases the yield and the content, and has short reaction time, simple and convenient operation and mild reaction conditions; and a reaction reagent is easy to recycle, so the improved method reaches the effects of lowering cost and reducing environment pollution.

Description

technical field [0001] The invention relates to a preparation method of a non-steroidal anti-inflammatory analgesic drug, in particular to a preparation method of aceclofenac. Background technique [0002] The chemical name of Aceclofenac is 2-(2,6-dichloroanilino)phenylacetoxyacetic acid, and its chemical structure is as follows: [0003] [0004] Developed by the Spanish Almirallprodesfarma pharmaceutical company, it was first listed in Spain in 1992, and it was included in the European Pharmacopoeia and the British Pharmacopoeia in 1998. This product is a powerful oral non-steroidal anti-inflammatory drug, suitable for the treatment of various rheumatoid arthritis and rheumatoid arthritis It is also suitable for pain and fever caused by various diseases. It is a safe and reliable drug for treating acute and chronic pain and anti-inflammation. It has strong anti-inflammatory and analgesic properties and few conventional anti-inflammatory and analgesic drugs Gastrointes...

Claims

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Application Information

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IPC IPC(8): C07C229/42C07C227/16A61P29/00
Inventor 赵志全张兰
Owner LUNAN PHARMA GROUP CORPORATION
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