Alkylation by secondary alcohols III: Fusion of medicinal sulfanilamides with benzhydrol

The fusion of certain sulfanilamides with benzhydrol in the presence of anhydrous zinc chloride affords several different products, depending primarily on the temperature at which the reaction is carried out. With sulfanilamide itself, three different products were isolated at 100, 160, and 180 degr...

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Bibliographic Details
Published inJournal of pharmaceutical sciences Vol. 64; no. 2; p. 292
Main Authors Moskalyk, R E, Malicky, J L
Format Journal Article
LanguageEnglish
Published United States 01.02.1975
Subjects
Alcohols
Alkylation
Aniline Compounds
Benzhydryl Compounds - chemical synthesis
Structure-Activity Relationship
Sulfacetamide
Sulfanilamides - chemical synthesis
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Summary:The fusion of certain sulfanilamides with benzhydrol in the presence of anhydrous zinc chloride affords several different products, depending primarily on the temperature at which the reaction is carried out. With sulfanilamide itself, three different products were isolated at 100, 160, and 180 degrees. A sequence of steps is suggested to account for the three products, one of which involves an intramolecular rearrangement of a benzhydryl moiety. The fusion of benzhydrol with p-toludine gives 2,6-dibenzhydrylaniline and not the N,N-dibenzhydryl derivative as previously reported.
ISSN:0022-3549
DOI:10.1002/jps.2600640221