Dear researchers,
Usually, the nucleophilic azidation can undergo with commercial available NaN3 with no further treatment. However, in some cases, the reaction requires NaN3 activated by hydrazine hydrate. Unfortunately, I havn't found any procedure on the internet, and none of my colleagues knows as well.
Does anyone knows how to activate NaN3 by hydrazine hydrate, please share a brief procedure and key points should be aware. Thanks for your generous help.
Yours sincerely,
Xu Zhaoxuan
Dear Zhaoxuan Xu, if it is a problem of reactivity, why not using sulfonyl azide or triflyl azide, or any alternative to them. Please have a look at the following documents. My Regards
https://doi.org/10.1021/ja062355+
https://doi.org/10.1021/ol701581g
Abdelkader BOUAZIZ Thanks for your advice. However, it was infeasible in some transformations. I have found methods to prepare activated sodium azide reported by Thiele (Ber. 1908, 41, 2681) and activation of commercially available salt by Nelles (Ber. 1932, 65, 1345). To avoid dangerous operations such as grinding sodium azide , the protocol can be simplified into the following procedure: dissolve commercially available salt into a minimum amount of 80% hydrazine hydrate, then precipitate with acetone, filtered, the filtrate was washed by methanol, then ether, afforded needle shaped crystal which can react with anhydride without solvent.
[Caution] The reaction of activated sodium azide without solvent might be violent, so please do not prepare azides whose Mw below 200 (that's why I haven't reply for months).
Happy to hear you bypassed your problem. We had a short experience in using sodium azide in the conversion of nitrile to tetrazole. We didn't encountred such problem of reactivity. Wish you the best of success.
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