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

  1. Klaus Banert1,
  2. Thomas M. Klapötke2,
  3. Stefan M. Sproll2

Article first published online: 28 NOV 2008

DOI: 10.1002/ejoc.200800764

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2009, Issue 2, pages 275–281, January 2009

Additional Information

How to Cite

Banert, K., Klapötke, T. M. and Sproll, S. M. (2009), Synthesis of N-[1-(2-Hydroxyethyl)-1H-tetrazol-5-yl]-N-methylhydrazine as Polymeric Precursor. Eur. J. Org. Chem., 2009: 275–281. doi: 10.1002/ejoc.200800764

Author Information

  1. 1

    Technische Universität Chemnitz, Straße der Nationen 62, 09111 Chemnitz, Germany, Fax: +49-371-531-21229

  2. 2

    Department of Chemistry and Biochemistry, University of Munich (LMU), Butenandtstr. 5–13, 81377 München, Germany, Fax: +49-89-2180-77492

Publication History

  1. Issue published online: 2 JAN 2009
  2. Article first published online: 28 NOV 2008
  3. Manuscript Received: 4 AUG 2008

Funded by

  • Ludwig-Maximilian University of Munich (LMU)
  • Fonds der Chemischen Industrie (FCI)
  • European Research Office (ERO) of the U.S. Army Research Laboratory (ARL) and the Armament Research, Development and Engineering Center (ARDEC). Grant Numbers: N 62558-05-C-0027, R&D1284-CH-01, R&D1285-CH-01, 9939-AN-01, W911NF-07-1-0569
  • Bundeswehr Research Institute for Materials, Explosives, Fuels and Lubricants (WIWEB). Grant Numbers: E/E210/4D004/X5143, E/E210/7D002/4F088

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Keywords:

  • Hydrazine;
  • Nitrogen heterocycles;
  • Nitrogen-rich compounds;
  • Polymers

Abstract

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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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