Synthesis of Sulfonyl Azides from Sulfonic Acids using Cyanuric Chloride

Authors(1) :-N. R. Pawase

A mild, efficient and convenient method for synthesis of sulfonyl azides from sulfonic acids is described. In situ sulfonyl chlorides are prepared from sulfonic acids. The sulfonyl chlorides were then further allowed to react with excess NaN3 in the same pot.

Authors and Affiliations

N. R. Pawase
Department of Chemistry, Padmashri Vikhe patil College, Pravaranagar (Loni kd.) Rahata, Ahmednagar, Gujarat, India

Sulfonyl Azides, Sulfonyl Chlorides, NaN3, N-Methyl

  1. I.B. Douglas, T.B. Johnson, J. Am. Chem. Soc. 1938, 60, 1486; A. Meinzer, A. Breckel, B.A. Thaher, N. Manicone, H.H. Otto, Helv. Chim. Acta 2004, 87, 90; H.I. skulnick, P.D. Johnson, P.A. Aristoff, J.k. Morris, K.D. Lovasz, W.J. Howe, K.D.Watenpaugh, M.N. janakiraman, D.J. Anderson, R.J. Reischer, T.M. Schwartz, L.S. Bannitt, P.K. Tomich, J.C. Lynn, M.M. Horng, K.T. Chong, R.R. Hinshaw, L.A. Dolak, E.P. Seest, F.J. Schwende, B.D. Rush, G.M. Howard, L.N. Toth, K.R. Wilkinson, T.J. Kakuk, C.W. Johnson, A.L. cole, R.M. Zaya, G.L. Zipp, p.L. Possert, R.J. Dalga, W.Z. Zhong, M.G. Williams, K.R. Romines, J. Med. Chem. 1997,40,1149; E. Vedejs, C. Kongkittingam, J. Org. Chem. 2000,65,2309; K.M. Youssef, E.Al-Abdullah, H. Ei-Khamees, Med. Chem. Res. 2001, 10, 404.
  2. A.M.Harned AM, W.M. Sherril, D.L. Flynn, P.R.Hanson, Tetrahedron. 2005, 61, 12093-12099.
  3. E.D. Goddard- Borger, R.V.Stick, Org Lett. 2007, 9, 3797-3800.
  4. P. Panchaud , L. Chabaud , Y.Landais , C. Ollivier, P.Renaud,S. Zigmantas, Chem Eur J. 2004, 10, 3606-3614.
  5. A.B.Charette , R.P. Wurz , T. Ollevier,? J. Org. Chem. 2000, 65, 9252-9254.
  6. D.F. Taber, R.E. Ruckle, M.J. Hennessy, J. Org. Chem. 1986, 51, 4077-4078.
  7. J. Waser, H.Nambu, E.M.Carreira, J. Am. Chem Soc. 2005, 127, 8294-8295.
  8. J.V. Ruppel, J.E Jones, C.A.Huff, R.M. Kamble, Y. Chen, X.P. Zhang, Org Lett. 2008, 10, 1995-1998.
  9. J. Waser, B.Gaspar, H. Nambu, E.M. Carreira, J. Am. Chem Soc. 2006, 128, 11693-11712.
  10. D.S. Masterson, J.P. Shackleford, Synlett. 2007, 8, 1302-1304.
  11. P. Panchaud, P. Renaud. Adv Synth Catal. 2004, 346, 925-928.
  12. R.A. Ei-Sayed, Phosphrous Sulfur Silicon Relat. Elem. 2004, 179, 237; N.G. Anderson, P.D. Ramsden, D. Che, M. Parvez, B.A. Keay, Org. Lett. 1999, 1, 2009; R.E. Harmon, G. Wellman, S.K. Gupta, J. Org. Chem. 1973, 38, 11; J.E. Leffler, Y. Tsuno, J. Org. Chem. 1963, 28, 902.
  13. J. Humlian, S. Gobec, Tetrahedron Lett. 2005, 46, 4069.
  14. S. Fujita, Synthesis 1982, 423.
  15. A. Barco, S. Benetti, P. Pollini, R. Tadia, Synthesis, 1974, 877; M. Frankel, P. Moses, Tetrahedron 1960, 9, 289.
  16. R. C. Reynolds, P.a. Crooks, J.A. Maddry, M.S. Akhtar, J.A. Montgomery, J.A. Secrist, J. Org. Chem. 1992, 57, 2983.
  17. G. Blotny, Tetrahedron Lett. 2003, 44, 1499.
  18. J. G. Kim, D.O. Jang, Synthesis 2008, 2885.
  19. B. Maleki, s. Hemmati, R. Tayebee, S. salami, Y. farokhzad, M. Baghayeri, F.m. Zonoz, E. Akbarzadeh, R. Moradi, A. Entezari, M.R. Abdi, S.S. Ashrafi, F. Taimazi, Helvetica Chimica acta. 2013, 96, 2147-2151.
  20. B.P. Bandgar, S.S. Pandit, Tetrahedron Lett. 2002, 43, 3413-3414.
  21. A. Kiani, B. Akhlaghinia, H. Rouchi- Saadabad, M. Bakavoli, Journal of Sulfur Chem. 2014, 35, 119-127.

Publication Details

Published in : Volume 3 | Issue 10 | November-December 2017
Date of Publication : 2017-12-31
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 09-11
Manuscript Number : IJSRST1731003
Publisher : Technoscience Academy

Print ISSN : 2395-6011, Online ISSN : 2395-602X

Cite This Article :

N. R. Pawase, " Synthesis of Sulfonyl Azides from Sulfonic Acids using Cyanuric Chloride", International Journal of Scientific Research in Science and Technology(IJSRST), Print ISSN : 2395-6011, Online ISSN : 2395-602X, Volume 3, Issue 10, pp.09-11, November-December-2017.
Journal URL : https://ijsrst.com/IJSRST1731003
Citation Detection and Elimination     |      | | BibTeX | RIS | CSV

Article Preview