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Synthesis method of diclofenac sodium impurities B

A technology of diclofenac sodium and impurities, applied in the field of drug synthesis, can solve the problems of difficult raw materials, high cost, low yield, etc., and achieve the effect of cheap raw materials, short steps and high product purity

Inactive Publication Date: 2018-05-18
ZHONGSHUAI PHARMA SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is to overcome the existing process for preparing diclofenac sodium impurity B, high cost, difficult to obtain raw materials, and low yield, and provide an effective method for preparing diclofenac sodium impurity B, the method provided by the invention The raw materials are cheap and easy to obtain, the steps are short, the reaction conditions are mild, the product purity is high, and the synthesis efficiency is high

Method used

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  • Synthesis method of diclofenac sodium impurities B
  • Synthesis method of diclofenac sodium impurities B
  • Synthesis method of diclofenac sodium impurities B

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0034] Synthesis of Example 1 Compound 2-[(2,6-dichlorophenyl)amino]toluene (intermediate 1)

[0035] Add 2,6-dichloroaniline (0.1mol), o-bromotoluene (0.1mol), potassium carbonate (0.3mol) and N,N-dimethylformamide (100ml) into a 250ml three-necked flask, stir and heat to 80°C, keep stirring for 4 hours, cool down to 20-25°C, pour the reaction system into 150ml of water, extract with ethyl acetate (200ml), separate, wash with water (150ml*2), dry over anhydrous sodium sulfate, and concentrate to obtain Crude product, directly vote for the next step.

Embodiment 2

[0036] Embodiment 2 compound 2-[(2,6-dichlorophenyl) amino] the synthesis of benzoic acid (intermediate 2)

[0037] Add the crude product obtained above, potassium permanganate (0.2mol) and 5% sodium hydroxide solution (200ml) into a 500ml three-neck flask, stir at room temperature for 6h, adjust the pH to 6 with dilute hydrochloric acid, and precipitate solids, filter and wash with water, After drying, 20.3 g of brown solid was obtained.

Embodiment 3

[0038] Synthesis of Example 3 Compound 2-[(2,6-dichlorophenyl)amino]benzyl alcohol (diclofenac sodium impurity C)

[0039] Add the above-prepared crude product (20.3g) and 100ml of tetrahydrofuran into a 250ml three-neck flask, stir, add 5.0g of lithium aluminum tetrahydride in batches, heat to 40°C, stir for 2h, cool down to 20°C, and pour the reaction system into 100ml of ice water, extracted with ethyl acetate (150ml*2), combined organic phases, washed with saturated sodium chloride solution (150ml), dried over anhydrous sodium sulfate, concentrated, column chromatography (petroleum ether: ethyl acetate = 20:1 ), to obtain 12.6g of white solid.

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Abstract

The invention discloses a synthesis method of diclofenac sodium impurities B. The method includes the following step that (1), 2,6-dichloroaniline and o-bromotuluene are condensed to obtain 2-[(2,6-dichloroanilino)amine]toluene under the alkaline action; (2), the 2-[(2,6-dichloroanilino)amine]toluene is oxidized with potassium permanganate to prepare 2-[(2,6-dichloroanilino)amine]benzoic acid; (3), the 2-[(2,6-dichloroanilino)amine]benzoic acid is reduced with lithium aluminum hydride to prepare 2-[(2,6-dichloroanilino)amine]benzyl alcohol; (4), the 2-[(2,6-dichloroanilino)amine]benzyl alcoholis oxidized with pyriddinium chlorochromate to obtain 2-[(2,6-dichloroanilino)amine]benzaldehyde. According to the synthesis method of the diclofenac sodium impurities B, the raw materials are low inprice and easy to obtain, steps are short, reaction conditions are mild, and operation is easy.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a method for preparing diclofenac sodium impurity B. Background technique [0002] Diclofenac sodium, also known as diclofenac, has a chemical name of 2-(2,6-dichloroanilino) sodium phenylacetate, and its structural formula is as follows: [0003] [0004] Diclofenac sodium is a non-steroidal powerful anti-inflammatory analgesic developed by Ciba-Geigy in Switzerland and listed in 1974. It is used for various rheumatoid arthritis, lupus erythematosus, neuritis and cancer, postoperative Pain and fever caused by various reasons. Because of its good curative effect, rapid oral absorption, fast excretion, long-term use without accumulation, and small individual differences, it has always been one of the best-selling drugs in the world, and it is also a key intermediate for the synthesis of other drugs such as aceclofenac. [0005] Drug impurity research has two important ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C223/06C07C213/00C07C215/68C07C227/02C07C229/58C07C209/10C07C211/52
CPCC07C209/10C07C213/00C07C221/00C07C227/02C07C223/06C07C215/68C07C229/58C07C211/52
Inventor 牛冰李书安刘杰李锐赵军霞周孟宇张新璐
Owner ZHONGSHUAI PHARMA SCI & TECH CO LTD
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