1-(2-Benzylaminophenyl)-2-phenylbenzimidazole

Ke-Qing Zhao, Ping Hu, Shi-Lin Zhao and Hong-Bo Xu

Department of Chemistry, Sichuan Normal University, Chengdu, 610066, P. R. China. Tel./Fax: 86-28-4764743. E-mail: [email protected]

Received: 13 May 2000 / Accepted:10 June 2000 / Published: 10 July 2000

When the imine-amine compound, bis[(2-benzylideneimino)phenyl]amine [1], is heated in presence of a transition metal salt (for example FeCl₃), a reaction occur leading to a new compound. After separation and characterization, we find it is a benzimidazole derivative, with a structure pattern frequently appearing in pharmaceutical molecules [1]. 0.5g red crystal of bis[(2-benzylideneimino)phenyl]amine is heated in ethanol for 30 minutes and changed into colorless. After cooling, 0.45g (90%) of white crystal product is collected by filtration.

M. p. 235 ^oC (ethanol).

¹H NMR (400 MHz, CDCl₃): 4.03 (t, J_HH=5.58Hz, 1H, NH), 4.24 (d, J_HH=5.58Hz, NCH₂), 6.6-8.0 (m, 18H, Ph).

¹³C NMR (75 MHz, CDCl₃): 47.0, 110.6, 112.1, 117.4, 119.8, 121.8, 123.1, 123.3, 126.7, 127.1, 128.4, 128.5, 128.6, 129.0, 129.6, 129.7, 130.4, 136.7, 138.4, 143.2, 143.9, 152.5.

IR (KBr): 3284, 3038, 2846, 1605, 1579.

Anal. Calc. for C₂₆H₂₁N₃ (375.50 ): C 83.16, H 5.65, N 11.19; Found: C 83.25, H 5.67, N 11.07.

References

1. Zhao, K.-Q.; Hu, P.; Li, Q.; Xu,  B.-H. Molecules 2000, 5, M167.
2. Wright, J. B. Chem. Rev. 1951, 48, 397-541.

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