Preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide

A technology of phenoxyphenyl and formamide acetyl, which is applied in the field of preparation of N-[4--5-hydroxy-2-phenoxyphenyl]methanesulfonamide, can solve the problem of unrecoverable NaI and serious environmental pollution , high production cost and other issues, to achieve the effect of low cost, high yield and reduced production cost

Pending Publication Date: 2021-10-22
佳尔科生物科技南通有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The hydrolysis of the methoxyl group is N-[4-(2-formamidoacetyl)-5-methoxy-2-phenoxyphenyl]methanesulfonamide in NaI / AlCl 3 / CH 3 Demethylation in CN system, the yield is less than 85%
This process uses expensive NaI, and the generated CH 3 I and excess NaI cannot be recovered, making the production cost very high and causing serious environmental pollution

Method used

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  • Preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide
  • Preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide

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Experimental program
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Effect test

Embodiment 1

[0021] Add 20g N-[4-(2-formylaminoacetyl)-5-methoxy-2-phenoxyphenyl]methanesulfonyl (produced by Jiaerke Biotechnology Nantong Co., Ltd.) and 250g DMF to the reaction flask Add 15.5g of NaBr; react at 140°C for 7 hours; after the reaction is completed, pour it into 500g of sodium sulfite solution with a mass ratio of 1%, a yellow solid is formed, filter with suction, wash with water, and dry in vacuo to obtain light yellow The solid compound was 17.9g, and the yield was 93%.

Embodiment 2

[0023] Add 20g N-[4-(2-formamidoacetyl)-5-methoxy-2-phenoxyphenyl]methanesulfonamide and 200gDMF to the reaction flask, then add 13.5gNaBr; react at 140°C , reaction time 7h; after the reaction was completed, it was poured into 500g mass ratio of 1% sodium sulfite solution, a yellow solid was generated, suction filtered, washed with water, and dried in vacuo to obtain 17.6g of light yellow solid compound with a yield of 91%.

Embodiment 3

[0025] Add 20g of N-[4-(2-formamidoacetyl)-5-methoxy-2-phenoxyphenyl]methanesulfonamide and 250g of DMF to the reaction flask, and then add 15.5g of NaBr. Put the reaction bottle in the ultrasonic generator, set the frequency at 25KHz; react at 140°C, the reaction time is 15min; pour the material into 500g of sodium sulfite solution with a mass ratio of 1%, a yellow solid is formed, suction filter, wash with water, vacuum After drying, 18.7 g of light yellow solid compound was obtained, with a yield of 97.1%.

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Abstract

The invention discloses a preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide. The preparation method comprises the following steps: with N-[4-(2-formylaminoacetyl)-5-methoxy-2-phenoloxyphenyl]methanesulfonamide as a raw material, dissolving the raw material in N,N-dimethylformamide (DMF) by using NaBr, and carrying out a demethylation reaction to obtain N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide. The preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide provided by the invention is friendly to environment, simple in process, high in yield and low in cost.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and relates to a new method for preparing N-[4-(2-formylaminoacetyl)-5-hydroxyl-2-phenoxyphenyl]methanesulfonamide. Background technique [0002] Iguratimod is a non-steroidal anti-inflammatory drug (NSAIDs), the chemical name is 3-carboxamido-7-methylsulfonamido-6-phenoxy-4H-1-benzopyran-4-one , a new type of disease-modifying drug (DMARDs) jointly developed by Toyama and Eisai Pharmaceutical Co., Ltd., for the treatment of rheumatoid arthritis (RA) and osteoarthritis (0A); compared with previous DMARDs , its effect is rapid, and its curative effect is equal to that of highly effective antirheumatic drugs (SAP, MTX), but its toxicity is low. This product can significantly reduce the inflammatory response, not only can selectively inhibit COX-2, but also can inhibit the production of inflammatory cytokines, tumor necrosis factor, lymphocytes and immunoglobulin, and has aut...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/08
CPCC07C303/40C07C311/08
Inventor 王彩霞周革
Owner 佳尔科生物科技南通有限公司
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