Chisholm - 14-4-2017 at 08:10
I have a substantial quantity of nitroguanidine (~300g), as well as sodium nitrite, zinc dust, and glacial acetic acid, and would like to perform some
experiments with derivatives of aminoguanidine.
Principally, I'm interested in salts of diazoaminotetrazole, like in this patent:
Attachment: US2064817.pdf (156kB)
This file has been downloaded 422 times
Procedures for aminoguanidine are in a couple of places; CoPaE has one, as does Org Syn, but I'd like a one-pot synthesis that obviates the need for
an intermediate filtering step.
The key concepts I'm seeing in all of the procedures are "keep the temperature below 40ºC" and "the reduction is complete when the yellow color
disappears."
The patent for sodium diazoaminotetrazolate involves adding aqueous nitrite to an aminoguanidine salt in acetate buffer solution.
The procedures I've seen for aminoguanidine involve acetic acid and zinc, and usually separate the aminoguanidine from the solution as the
nearly-insoluble bicarbonate.
Could a one-pot procedure be developed here that prevents precipitation of the zinc?
PHILOU Zrealone - 14-4-2017 at 18:50
Maybe the fact that Zn(2+) is complexated by NH3, N2H4 related molecules....will cause troubles
Zn(OH)2 + 4 NH3 <--==> Zn(NH3)4(OH)2 (soluble)
Zn(OH)2 + 2 H2N-NH2 <--==> Zn(N2H4)2(OH)2 (unsoluble IIRC)