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Short Note

1-Benzimidazolyl-1-benztriazolylmethane

by
Milata Viktor
* and
Kada Rudolf
Department of Organic Chemistry, Faculty of Chemical Technology, Slovak University of Technology, Radlinskeho 9, SK-812 37 Bratislava, Slovak Republic
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(5), M12; https://doi.org/10.3390/M12
Submission received: 7 May 1997 / Published: 26 May 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 02 m12 i001
Symmetrically substituted bis(azolyl)methanes are often prepared from azoles in dichloromethane under PTC conditions [1]. Unsymmetrically substituted 1-benztriazolylmethanes can be prepared from 1-hydroxymethylbenzotriazole [2] via nucleophilic substitution with secondary amines, in this case, benzimidazole.
1-Hydroxymethylbenzotriazole (2.98 g, 20 mmol) was dissolved in warm ethanol (50 ml). Benzimidazole (2.36 g, 20 mmol) was then added and the mixture was heated at reflux temperature. The reaction was monitored by TLC. After the reaction had ended the reaction mixture was set aside at 5 deg.C overnight. The crystalline product was then collected, washed with cold ether and recrystallized from ethanol. Yield 4.18 g (84.0 %) of a white crystalline powder.
M.p. 92-93 deg.C.
TLC (EtOAc): Rf 0.30.
1H NMR (CDCl3): 8.28 (s, 1H, -CH=), 7.00-8.13 (m, 8H, Harom), 6.05 (s, 1H, CH2), 5.63 (s, 1H, CH2).
IR (cm-1, KBr): 3179, 3115, 3096, 3063, 3001, 2965, 2863, 2797, 2741, 1458, 1408, 1306, 1273, 1246, 1235, 1159, 1076, 783, 768, 747, 619.
UV (lmax/log ε, methanol): 244/3.03, 250/3.05, 272/3.09, 279/3.06.
Anal. calc. for C14H11N5 (249.0): C 67.47, H 4.42, N 28.10; found: C 67.17, H 4.30, N 27.84.

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgements

The authors would like to thank Slovak Grant Agency (financial support No. 95/5195/202).

References and Notes

  1. Julia, S.; Sala, P.; del Mazo, J.; Sancho, M.; Ochoa, C.; Elguero, J.; Fayet, J.P.; Vertut, M.C. N-Polyazo- lylmethanes. 1. Synthesis and NMR study of N,N-diazolylmethanes. J. Heterocycl. Chem. 1982, 19, 1141. [Google Scholar] [CrossRef]
  2. Fries, K.; Guterbock, H.; Kuhn, H. Untersuchungen in der Reihe des Azimidobenzols und des N-Methyl-Azimidobenzols. Ann. 1934, 511, 213. [Google Scholar] [CrossRef]
  • Sample Availability: Available from the author, 2g.

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MDPI and ACS Style

Viktor, M.; Rudolf, K. 1-Benzimidazolyl-1-benztriazolylmethane. Molecules 1997, 2, M12. https://doi.org/10.3390/M12

AMA Style

Viktor M, Rudolf K. 1-Benzimidazolyl-1-benztriazolylmethane. Molecules. 1997; 2(5):M12. https://doi.org/10.3390/M12

Chicago/Turabian Style

Viktor, Milata, and Kada Rudolf. 1997. "1-Benzimidazolyl-1-benztriazolylmethane" Molecules 2, no. 5: M12. https://doi.org/10.3390/M12

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