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New reactions of N ‐ T ‐butyl‐ N ‐benzoylhydrazine with triphosgene
Author(s) -
QingMin Wang,
JunRan Cheng,
RunQiu Huang
Publication year - 2003
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.5570400130
Subject(s) - triphosgene , triethylamine , chemistry , yield (engineering) , pentamer , base (topology) , medicinal chemistry , organic chemistry , mathematics , mathematical analysis , biochemistry , materials science , metallurgy , phosgene
N ‐ tert ‐Butyl‐ N ‐benzoylhydrazine was prepared in a new and convenient procedure with good yield. Triphosgene underwent reaction with three equivalents of N ‐ t ‐butyl‐ N ‐benzoylhydrazine using six equivalents of triethylamine as a base to yield the cyclic tetramer of N ‐ t ‐butyl‐ N ‐isocyanatobenzoylamide. Treatment of triphosgene with three equivalents of N ‐ t ‐butyl‐ N ‐benzoylhydrazine either in the presence of three equivalents of triethylamine or in the absence of triethylamine afforded the cyclic pentamer of iso‐cyanate, from which tert ‐butyl is eliminated.