Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom