View More View Less
  • 1 Sigma-Aldrich Production GmbH, 9471, Industriestrasse 25, Buchs, Switzerland
Restricted access

Abstract

The synthesis and utilisation of acyl azides in a flow apparatus combined with an automated extraction unit is described. This process safely provides multi-100 g quantities of a labile diacyl azide (3) as an intermediate that could not be generated safely by classic batch methods. Its subsequent conversion to the desired amine (4) represents an example for process intensification. The same set-up with an output capacity of >30 g/h was used for the unattended synthesis of benzoyl azide as the final product in solution (tert-butyl methyl ether (TBME), 0.5 M).

  • 1. K. Jähnisch V. Hessel H. Löwe M. Baerns 2004 Angew. Chem. Int. Ed 43 406446.

  • 2. Fukuyama, T.; Rahman, M. T.; Sato, M.; Ryu, I. Synlett 2008, 151163.

  • 3. T. Schwalbe V. Autze G. Wille 2002 Chimia 56 636646.

  • 4. B. Ahmed-Omer D. Barrow T. Wirth 2009 Tetrahedron Lett 50 33523355.

  • 5. B. Ahmed-Omer D. Barrow T. Wirth 2008 Chem. Eng. J 135S S280S283.

  • 6. Ueno, M.; Hisamoto, H.; Kitamori, T.; Kobayashi, S. Chem. Commun. 2003, 936937.

  • 7. R. C. Wheeler O. Benali M. Deal E. Farrant S. J. F. MacDonald B. H. Warrington 2007 Org. Proc. Res. Dev 11 704710.

  • 8. H. Song D. L. Chen R. F. Ismagilov 2006 45 73367356.

  • 9. M. N. Kashid L. Kiwi-Minsker 2009 Ind. Eng. Chem. Res 48 64656485.

  • 10. A. McKillop J. C. Fiaud R. P. Hug 1974 Tetrahedron 30 13791382.

  • 11. G. D. Yadav P. M. Bisht 2004 Catalysis Comm 5 259263.

  • 12. G. D. Yadav N. M. Desai 2006 Catalysis Comm 7 325330.

  • 13. M. Riccaboni E. La Porta A. Martorana R. Attanasio 2010 Tetrahedron 66 40324039.