O-Phenylenediamine → N,N-bis(1H-benzimidazol-2-ylmethyl)-N-benzylamine

Participants

Reaction Steps

2d was synthesised by an analogous procedure to that described for 2a using o-phenylenediamine (2.41 g, 22.34 mmol) and benzyliminodiacetic acid (4.10 g, 11.17 mmol) in ethyleneglycol (10 ml) at 190° C. Yield 3.50 g (85%). 1H NMR (250.13 MHz, DMSO-d6, r.t.), δ 3.74 (s, 2H, CH2), 3.97 (s, 4H, NCH2), 7.19-7.58 (overlapping and broad m, 13H, ArH). 13C NMR (100.6 MHz, MeOH-d4, r.t.), δ 56.24 (NCH2), 62.34 (CH2), 102.03 (ArC), 126.94 (ArC), 132.37 (ArC), 133.38 (ArC), 134.23 (ArC), 142.70 (ArCq), 143.47 (ArCq), 157.41 (ArCq). +CI MS (m/z): 367 ([MH+]).

Provenance & Evidence