Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1975-05-21
1976-10-19
Ford, John M.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07D27902
Patent
active
039870383
ABSTRACT:
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}eth anone 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-acetamid e 1,1-dioxide (I) is reacted with an alkali metal alkoxide of a lower alcohol in an inert solvent at temperatures below 30.degree. C. to form the benzenesulfonylglycineamide, alkyl 2-{[({[(5-methyl-3-isoxazolyl)amino]carbonyl}methyl)amino]sulfonyl}benzoat e (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.degree. C. to 70.degree. C. to form the desired oxadiazole compound III.
REFERENCES:
patent: 3787324 (1974-01-01), Zinnes et al.
patent: 3822258 (1974-07-01), Zinnes et al.
patent: 3868367 (1975-02-01), Zinnes et al.
Fabian Arthur C.
Genzer Jerome D.
Kasulanis Charles Francis
Shavel, Jr. John
Zinnes Harold
Chow Frank S.
Ford John M.
Graddis Albert H.
Kelly Anne M.
Warner-Lambert & Company
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