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A convenient synthesis of N , 5‐disubstituted‐4‐imidazoline‐2‐thiones
Author(s) -
Doney Jeffrey J.,
Altland Henry W.
Publication year - 1979
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.5570160543
Subject(s) - chemistry , imidazoline receptor , triethylamine , thiourea , isothiocyanate , ketone , toluene , hydrochloride , medicinal chemistry , organic chemistry , medicine
The preparation of N ,5‐disubstituted‐4‐imidazoline‐2‐thiones from readily obtainable starting materials is described. These imidazolines are synthesized by refluxing in toluene the appropriate 2‐aminomethyl ketone hydrochloride with an equivalent of the desired isothiocyanate and an equivalent of triethylamine. The intermediate thiourea spontaneously eliminates water (removed from the reaction medium by a Dean‐Stark trap) to form the imidazoline thione.