CHLOROSULFONATION OF N-PHENYLMORPHOLINE, BENZOTHIAZOLE, 2-METHYL BENZOTHIAZOLE AND TRIPHENYLOXAZOLE

N-Phenylmorpholine ( 1 ) reacted with chlorosulfonic acid to give the p-sulfonyl chloride ( 2 ), which was characterized as the sulfonamides ( 3 - 5 ). Benzothiazole ( 6 ) was converted into the sulfonyl chloride ( 7 ) by sequential treatment with hot chlorosulfonic acid and thionyl chloride. Reaction of ( 7 ) with amines afforded the derivatives ( 8 - 10 ); NMR spectral analysis of the dimethylamide ( 8 ) indicated that it was a mixture of the 4- and 7-isomers. Chlorosulfonation of 2-methylbenzothiazole ( 11 ) was achieved by heating with chlorosulfonic acid with or without thionyl chloride. The chloride ( 12 ) was converted into amides ( 13 - 19 ). Study of the NMR spectra indicated that mixtures of the 5- and 6-isomers were formed. 2,4,5-Triphenyloxazole ( 20 ) reacted with chlorosulfonic acid to give either the mono-( 21 ), bis ( 23 ) or bis-tris sulfonylchlorides ( 23 , 34 ); these were converted into 14 sulfonamides. 2-(p-Nitrophenyl)-4,5-diphenyloxazole ( 41 ) reacted with hot chlorosulfonic acid to give the bis-sulfonyl chloride ( 42 ), characterized as the dimethylsulfonamide ( 43 ). Attempts to form the pure monosulfonyl chloride and to mono nitrate 2,4,5-triphenyloxazole ( 20 ) were unsuccessful.