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Synthesis of a 2‐Methyl‐4‐sulfanilamido‐s‐triazine derivative
Author(s) -
Kametani Tetsuji,
Okui Kiyoshi,
Koizumi Masuo
Publication year - 1972
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.5570090509
Subject(s) - chemistry , raney nickel , sodium hydroxide , guanidine , triazine , pyridine , medicinal chemistry , trimethylamine , derivative (finance) , hydrolysis , benzene , aqueous solution , chloride , condensation , organic chemistry , nuclear chemistry , hydrogen , financial economics , economics , thermodynamics , physics
An attempt to obtain 2‐methyl‐4‐sulfanilamido‐s‐triazine (XXI) by condensation of 2‐amino‐4‐methyl‐ s ‐triazine (II) with p ‐acetamidobenzenesulfonyl chloride (III) in pyridine and in benzene containing trimethylamine gave instead the unexpected products, guanidine N ‐acetylsulfanilate (IV) (after hydrolysis) and N 1 , N 1 ‐dimethylsulfanilamide (V), respectively. On the other hand, 2‐methyl‐4‐methylthio‐6‐sulfanilamido‐s‐triazine (XIX) was obtained from 4,6‐dimethylthio‐ s ‐triazine (XVII), but the reduction of XIX with Raney nickel in aqueous sodium hydroxide solution also gave an unexpected compound, sulfaguanidine (XX).