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Synthesis of heterocyclic compounds from o ‐aminobenzenethiol and ammonium thiocarbamate
Author(s) -
D'Amico John J.,
Fuhrhop Ralph W.,
Bollinger Frederic G.,
Dahl William E.
Publication year - 1986
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.5570230301
Subject(s) - thiocarbamate , chemistry , triethylamine , yield (engineering) , sulfide , ammonium , carbonyl sulfide , medicinal chemistry , oxalate , mass spectrum , organic chemistry , sulfur , ion , materials science , metallurgy
The reaction of o ‐aminobenzenethiol with carbonyl sulfide in the presence of triethylamine afforded an alternate route for the synthesis of 2‐benzothiazolinone ( 1 ) in 97–98% yield. The reaction of ammonium thiocarbamate ( 2 ) with 2‐chlorocyclohexanone furnished the novel 4,5,6,7‐tetrahydro‐2‐benzothiazolinone ( 3 ). 3‐Ethoxy‐2 H ‐1,4‐benzothiazin‐2‐one ( 7 ) was prepared by the reaction of o ‐aminobenzenethiol with diethyl oxalate. Possible pathways and supporting nmr, ir and mass spectra are discussed.