Improved reaction conditions for the preparation of ydro-5-imino-2-(ni
troimino)imidazo[4,5-d]imidazole (3) from 4,5-dihydroxy-2-nitroiminoim
idazolidine (2) and guanidine hydrochloride are described. Treatment o
f the hydrochloride salt of 3 with nitric acid at low temperature gene
rates the nitrate salt of 3 and not tahydro-2,5-bis(nitroimino)imidazo
[4,5-d]imidazole (1a) as previously reported. The bis(nitroimino) comp
ound (1a) was obtained by slow addition of nitric acid to a mixture of
the monohydrochloride salt of the bicyclic guanidine (3) and acetic a
nhydride.