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Synthesis of heterocyclic compounds from 3‐acetyl‐3‐chloropropyl acetate
Author(s) -
D'Amico John J.,
Bellinger Frederic G.,
Thompson Michael,
Freeman John J.,
Dahl William E.,
Pustinger John V.
Publication year - 1988
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.5570250429
Subject(s) - chemistry , dithiocarbamate , ammonium acetate , isocyanate , salt (chemistry) , ring (chemistry) , potassium , medicinal chemistry , mass spectrum , organic chemistry , ammonium , polyurethane , high performance liquid chromatography , ion
The reaction of the potassium salt of 2‐mercaptobenzimidazole with 3‐acetyl‐3‐chloropropyl acetate afforded the novel heterocyclic compound 1 . When solutions of 1 in deuteriodimethylsulfoxide or deuteriomethanol were allowed to stand at room temperatures for 15 minutes and 19 days, respectively, ring opening of 1 occurred to give the precursor, 3‐acetyl‐3‐(2‐benzimidazolthio)propyl‐1‐ol. The treatment of 1 with p ‐fluorophenyl isocyanate furnished the carbanilate 2 . The reaction of ammonium dithiocarbamate with the above chloroketone afforded the 2‐thiazolethione 3 . Possible mechanisms and supporting nmr, ir, mass spectral data for 1–3 and single crystal X‐ray analysis for 2 are discussed.
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