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

HRID 1645199Notes

Reaction equation

HRID 1645199 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][N:10]([CH2:15][C:16](O)=O)[CH2:11][C:12](O)=O>C(O)CO>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=[C:12]1[CH2:11][N:10]([CH2:15][C:16]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[CH3:9]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 20441N-methyliminodiacetic acid

Product 1

HCID 59460N,N-bis(1H-benzimidazol-2-ylmethyl)-N-methylamine

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

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+]).

Sources & evidence

ORD record
ord-933e78fbf7c44e71adac51346ae4eefd
Source dataset
uspto-grants-2012_02
Patent number
US08124698B2

Reaction notes

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