Synthesis of N-[1-(2-Hydroxyethyl)-1H-tetrazol-5-yl]-N-methylhydrazine as Polymeric Precursor

A nitrogen-rich Polymer was formed from the reaction of hexamethylene diisocyanate and N-[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]-N-methylhydrazine (3) monomers. Compound 3 was synthesized by a nucleophilic substitution of the methylated sulfur atom of 4-[2-(acetoxy)ethyl]-2-methylthiosemicarbazide (10) with sodium azide and final deprotection of the formed N-[1-2-(acetoxyethyl)-1H-tetrazol-5-yl]-N-methylhydrazine (13), Moreover, the isomer 4-(2-azidoethyl)-2-methylsemicarbazide (18) to 3 was synthesized. Compounds 3, 10, 13 and 4-[2-(trimethylsilyloxy)ethyl]-2-methylthiosemicarbazide (15) were characterized by using vibrational spectroscopy (IR, Raman), mass spectrometry and multinuclear NMR spectroscopy. The crystal structures of 3, 10 and 13 were determined by using single-crystal X-ray diffraction. The molecular weights of the polymers were determined by GPC. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)