Premium
Synthesis and structure elucidation of 3‐methoxy‐1‐methyl‐1 H ‐1,2,4,‐triazol‐5‐amine and 5‐methoxy‐1‐methyl‐1 H‐ 1,2,4,‐triazol‐3‐amine
Author(s) -
Selby T. P.,
Lepone G. E.
Publication year - 1984
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.5570210114
Subject(s) - chemistry , methylhydrazine , amine gas treating , structural isomer , adduct , medicinal chemistry , hydrazine (antidepressant) , triazole , yield (engineering) , isocyanate , stereochemistry , organic chemistry , phenylhydrazine , materials science , chromatography , metallurgy , polyurethane
Previously it was shown that condensation of dimethyl N ‐cyanodithioimidocarbonate ( 1a ) with methylhydrazine gave predominantly 1‐methyl‐5‐methylthio‐1 H ‐,2,4‐triazol‐3‐amine ( 2 ), which was initially identified erroneously as the regioisomer l‐methyl‐3‐methylthio‐1 H ‐1,2,4‐triazol‐5‐amine ( 3 ). We have found that reaction of dimethyl N ‐cyanoimidocarbonate ( 1b ) with methyl hydrazine affords a high yield of 3‐methoxy‐1‐methyl‐1 H ‐1,2,4‐triazol‐5‐amine ( 4 ) rather than the regioisomer 5‐methoxy‐1‐methyl‐1 H‐ 1,2,4‐triazol‐3‐amine ( 5 ). The structure assignment of 4 was confirmed by X‐ray crystallographic analysis of the benzenesulfonyl isocyanate adduct 7 . Triazole 5 was obtained after reacting dimethyl N ‐cyanothioimidocarbonate ( 1c ) with methylhydrazine.