C - Chemistry – Metallurgy – 07 – F
Patent
C - Chemistry, Metallurgy
07
F
402/13, 403/29,
C07F 7/10 (2006.01) C08G 77/26 (2006.01) C08G 77/388 (2006.01) C08J 9/00 (2006.01)
Patent
CA 1080709
Abstract of the Disclosure This invention relates to a process for the preparation of 1- {[5-(4-hydroxy-2H-1,2-benzothiazin-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-isoxazolylcarbamoyl)- 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.
254798
Kanner Bernard
Prokai Bela
Na
Union Carbide Corporation
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