Process for the preparation of...

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C - Chemistry, Metallurgy

07

D

260/243.21

C07D 417/04 (2006.01) C07D 261/14 (2006.01)

Patent

CA 1080708

Abstract of the Disclosure This invention relates to a process for the preparations of 1- ([5-(4-hydroxy-2H-1,2-ben?othiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl)ethanone S,S-dioxide (III), a novel intermediate useful in the preparation of the known anti-inflammatory, agent,4-hydroxy-3-(5-methyl-3-isoxazolyl)- 2-methyl-2H-1,2-benzothiazine 1,1-dioxide (IV). According to the process of this invention, the saccharin compound, 2,3-dihydro-N-(5-methyl-3-isoxazolyl)- 3-oxo-1,2-benzisothiazole-2-acetamide 1,1-dioxide (I) is reacted with an alkali metal alkoxide of a lower alcohol in an inert solvent at temperatures below 30°C. to form the benzenesulfonylglycineamide, alkyl 2-{[({[(5-methyl- 3-isoxazolyl)amino]carbonyl]methyl)amino]sulfonyl)benzoate (II), which is ring closed and rearranged by reaction with an alkali metal alkoxide of a lower alcohol in an inert solvent at temperatures of from 60°C. to 70°C. to form the desired oxadiazole compound III.

252911

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