Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: H2NNH2 on July 21, 2009, 08:59:40 PM

Title: Acetylation of Hydrazine
Post by: H2NNH2 on July 21, 2009, 08:59:40 PM

Greetings all,
   I was hoping to synthesise acetic hydrazide using hydrazine sulphate and acetic anhydride  (2:1 equivalents, respectively) in ethanol. However, a test reaction where I added triethylamine and stirring for several hours did not seem to yield the appropriate product by TLC.

Title: Re: Acetylation of Hydrazine
Post by: H2NNH2 on July 21, 2009, 10:56:20 PM

And for some reason the second part of my post did not appear online...

Anyway, I was curious what public opinion recommended for my next reaction. I had it in mind to try adding NaOH to the hydrazine sulfate, then add the Ethanol and acetic anhydride, allowing the reaction to proceed for a "period" of time. Unfortunately I am limited to the sulfate salt because I have to ¹⁵N label acetic hydrazide and purchasing hydrazine hydrate is ridiculously expensive (350 USD for 500 mg of the sulphate versus 1000 USD for 100mg of the hydrate [SIGMA])

Any recommendations? Hopefully the amount of actual hydrazine I generate will not be terribly dangerous or refractory (100 mg hydrazine sulfate).

Thanks!