62547-03-9Relevant articles and documents
SOME SULFONYL DERIVATIVES OF SALICYLIC ACID AND RELATED COMPOUNDS
Cremlyn, Richard,Swinbourne, Frederick,Atherall, John,Courtney, Lynn,Cronje, Theo,at al.
, p. 155 - 164 (2007/10/02)
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.
