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

HRID 1645201Notes

Reaction equation

HRID 1645201 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH2:9]([N:16]([CH2:21][C:22](O)=O)[CH2:17][C:18](O)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)CO>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=[C:18]1[CH2:17][N:16]([CH2:21][C:22]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 77606N-Benzylaminodiacetic acid

Product 1

HCID 21107922N,N-bis(1H-benzimidazol-2-ylmethyl)-N-benzylamine

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

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+]).

Workup

  1. customat 190° C

Sources & evidence

ORD record
ord-c68646c4fb83446e97e4e42b94283a5b
Source dataset
uspto-grants-2012_02
Patent number
US08124698B2

Reaction notes

Loading…