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Abstract
o-Methoxybenzamide, salicyclic acid, salicylamide and N-acetylsalicylamide have been converted to the corresponding 5-sulfonyl chlorides, and p-hydroxybenzoic acid to the 3-sulfonyl chloride. The sulfonyl chlorides were characterized by the preparation of various derivatives, e.g. amides, hydrazides, hydrazones and azides. Chlorosulfonation of O-acetyl compounds showed either complete or partial deacetylation. O-Acetyl compounds were therefore obtained by subsequent acetylation. O-Acetylsalicylamide on heating was converted to the N-acetyl derivative and the isomerization was followed by h.p.l.c. In contrast both m-and p-acetoxybenzamides were relatively stable. Salicylanilide and O-methylsalicylanilide, with chlorosulfonic acid gave the 1,4′-disulfonyl chlorides. On the other hand, 4′-chloro- and 4′-chloro-O-methyl-salicylanilides afforded the corresponding monosulfonyl chlorides. The i.r., n.m.r. and mass spectra, together with the algaecidal and antibacterial results are briefly discussed.