Mephisto
Chemicus Diabolicus
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Registered: 24-8-2002
Location: Germany
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Method for making 5-aminotetrazole from aminoguanidine bicarbonate?
Has someone a description for making 5-aminotetrazole? The starting material could be aminoguanidine bicarbonate or nitroguanidine (I know the methods
from hydrazine and cyanamide, so please don’t post them.). I’ll be lucky for a detailed process (e.g. heat XY g of this stuff with ...).
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Nick F
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I have a large amount of aminotetrazole, so if you want to know anything about its properties, ask.
Unfortunately, I did not make it myself.
I do not know the exact method, but aminoguanidine is diazotised with NaNO2 in the presence of a mineral acid (ie, HCl, not acetic, as when making
tetrazene) to form guanyl azide. Guanyl azide, on treatment with acids or weak bases, undergoes cyclisation to form 5-aminotetrazole.
Although the same reference said that guanyl azide was first isolated as its nitrate salt. So perhaps you have to heat it with acids or weak bases, it
is not clear.
That's about all the info I could find. That's from COPAE.
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Mephisto
Chemicus Diabolicus
Posts: 295
Registered: 24-8-2002
Location: Germany
Member Is Offline
Mood: swinging
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Nick F: Thank you for your offer! Maybe I’ll use it some time later.
I found, that I can use this processes, which start with hydrazine and cyanamide. A aminoguanidine salt is formed as an intermediate-product. So at
this point I can start. The only problem is to calculate the quantity of the aminoguanidine salt which has formed, because I don’t know the
yield of the intermediate-product and it isn’t 100%. It can be approximately estimate, so I thing it’s good enough for me. I will use U.S.
patent 5,594,146, if someone else is interested in this synthesis.
And if someone knows a better way, it can be still posted here.
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Nick F
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Aha! I've just remembered that I collected most of the useful information that I could find on 5-ATZ, and posted it on www.roguesci.org/theforum. Go to the Links & Literature section, then the Patents topic, and look about half way down the first page.
Azides will also undergo addition with nitriles to form tetrazoles (5-H, 5-amino, 5-alkyl etc).
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