Bis[(2-benzylideneimino)phenyl]amine

Imine and amine ligands have been widely used in the field of transition metal catalyzed olefin polymerization [1]. Here we report the synthesis of a tri-dendated imine-amine compound which we plan to use as a ligand. bis(2-Aminophenyl)amine (0.5g, 2.5mmol) [2] and benzaldehyde (0.53ml, 5.2mmol) are added into 10ml of CH₂Cl₂ and refluxed 4h under N₂. The mixture is concentrated in vacuo, washed with cold hexane and dried in vacuo to give a red crystal product, 0.8g (yield 90%).

M. p. 195°C.

¹H NMR (400 MHz, CDCl₃): 8.23 (s, 1H, NH), 8.55 (s, 2H, N=CH), 6.8-8.0 (m, 18H, Ph).

¹³C NMR (75 MHz, CDCl₃): Ar, 114.4, 119.8, 127.3, 128.6, 128.8, 131.1, 136.3, 137.7, 139.3; C=N, 157.9.

IR (KBr): 3350, 3051, 2873, 1622, 1582.

Anal. Calc. for C₂₆H₂₁N₃ (375.50): C 83.16, H 5.65, N 11.19; Found: C 83.04, H 5.67, N 11.29.