Download PDF
Synlett 2010(13): 2045-2046  
DOI: 10.1055/s-0030-1258508
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Bis(benzotriazolyl)methanethione

Archana Singh*
Senior Research Fellow, Department of Chemistry, Faculty of ­Science, Banaras Hindu University, Varanasi 221005, India
e-Mail: archana_chembhu@yahoo.co.in;
Further Information

Publication History

Publication Date:
28 July 2010 (online)

   Permissions and Reprints All articles of this category

Introduction

Bis(benzotriazolyl)methanethione, a reagent derived from benzotriazole, is a thiophosgene equivalent for thioacylations and for the synthesis of different thiocarbonyl compounds. [¹] [²] Compared to thiophosgene, bis- (benzotriazolyl)methanethione is found to be more advantageous due to its high stability and less toxicity. It is a crystalline solid, easy to handle, and it can be stored for years at room temperature. Bis(benzotriazolyl)methan­ethione can be obtained in high yield as yellow crystals (mp 170-171 ˚C) starting from benzotriazole (Scheme  [¹] ). [³]

Scheme 1

    References

  • 1a Katritzky AR. Belyakov SA. Aldrichimica Acta  1998,  31:  35 
    Google Scholar
  • 1b Katritzky AR. Lan X. Yang JZ. Denisko OV. Chem. Rev.  1998,  98:  409 
    Google Scholar
  • 2 Katritzky AR. Witek RM. Rodriguez-Garcia V. Mohapatra PP. Rogers JW. Cusido J. Abdel-Fattah AAA. Steel PJ. J. Org. Chem.  2005,  70:  7866 
    Google Scholar
  • 3 Orth RE. Soedigdo S. J. Heterocycl. Chem.  1965,  2:  486 
    CrossrefGoogle Scholar
  • 4 Katritzky AR. Ledoux S. Witek RM. Nair SK. J. Org. Chem.  2004,  69:  2976 
    Google Scholar
  • 5a Tiwari VK. Singh DD. Hussain HA. Mishra BB. Singh A. Monatsh. Chem.  2008,  139:  43 
    Google Scholar
  • 5b Tiwari VK. Kale RR. Mishra BB. Singh A. ARKIVOC  2008,  (xiv):  27 
    Google Scholar
  • 6a Tiwari VK. Singh A. Hussain HA. Mishra BB. Tripathi VJ. Monatsh. Chem.  2007,  138:  653 
    Google Scholar
  • 6b Singh A. Kate RR. Tiwari VK. Trends in Carbohydrate Research   2009,  1:  80 
    Google Scholar
  • 7 Katritzky AR. Khashab NM. Bobrov S. Yoshioka M. J. Org. Chem.  2006,  71:  6753 
    CrossrefGoogle Scholar
  • 8 Katritzky AR. Khashab NM. Gromova AV. ARKIVOC  2006,  (iii):  226 
    Google Scholar
  • 9 Larsen C. Harpp DN. J. Org. Chem.  1980,  45:  3713 
    CrossrefGoogle Scholar
  • 10 Katritzky AR. Khashab NM. Bobrov S. Helv. Chim. Acta  2005,  88:  1664 
    CrossrefGoogle Scholar
  • 11 Sasmal PK. Sridhar S. Iqbal J. Tetrahedron Lett.  2006,  47:  8661 
    CrossrefGoogle Scholar