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Chlorosulfonation of 2‐arylimidazoles
Author(s) -
Baldwin J. J.,
Lumma P. K.,
Ponticello G. S.,
Novello F. C.,
Sprague J. M.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140533
Subject(s) - chemistry , imidazole , substituent , sulfonyl , aryl , ring (chemistry) , amide , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
Abstract The chlorosulfonation of 2‐arylimidazoles was investigated; the resulting sulfonyl chloride derivatives were isolated and characterized as the corresponding sulfonamides. When the 2‐aryl substituent was 3,4‐dichlorophenyl or 3‐pyridyl, chlorosulfonation occurred only on the imidazole ring. The chlorosulfonation of 2‐(4‐chlorophenyl)imidazole was temperature dependent, yielding either a mono or disulfonamide after treatment with ammonia. The structure of this disulfon‐amide was determined from pmr spectra to be 2‐(4‐chloro‐3‐sulfamoyl)‐4(5)sulfamoylimidazole.