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

Participants

Reaction Steps

2b was synthesised by an analogous procedure to that described for 2a using o-phenylenediamine (5.88 g, 54.40 mmol) and methyliminodiacetic acid (4.00 g, 27.2 mmol) in ethyleneglycol (20 ml). Yield 6.88 g (87%). 1H NMR (250.13 MHz, CD3OD, r.t.), δ 2.29 (s, 3H, NCH3), 3.92 (s, 4H, N(CH2)), 7.19-7.23 (m, J3=3.35 Hz, 4H, ArH), 7.52-7.56 (m, J3=3.35 Hz, 4H, ArH). 13C NMR (62.9 MHz, DMSO-d6, r.t.) δ 47.31 (CH3), 59.97 (NCH2), 126.66 (ArC), 157.45 (ArCq). Anal. Calc. for C17H17N5 (in %) C, 70.10; H, 5.84; N, 24.05. Found C, 70.22; H, 6.05; N, 23.76. +CI MS: (m/z): 292 ([MH+]).

Provenance & Evidence