O-Phenylenediamine → (E)-2-[2-(3,4-Dimethoxyphenyl)-vinyl]-1H-benzoimidazole

HRID 1278720Notes

Reaction equation

HRID 1278720 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Cl.CO[C:12](=N)[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1.O.Cl>CO>[CH3:24][O:23][C:17]1[CH:16]=[C:15](/[CH:14]=[CH:13]/[C:12]2[NH:8][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[N:7]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 21885828Hydrate;hydrochlorideHCID 86758495Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride

Product 1

HCID 5834650(E)-2-[2-(3,4-Dimethoxyphenyl)-vinyl]-1H-benzoimidazoleYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1,2-phenylenediamine (0.63 g; 5.8 mmol) and methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride (1.5 g; 5.8 mmol) in methanol (35 mL) was stirred at ambient temperature for 18 hours. The methanol solution was concentrated to dryness. The residue was recrystallized from MeOH-Diethyl Ether to obtain 1.3 g (67% yield) of the title compound as a mono-hydrochloride, hydrate, yellow solid, m.p. 248° C. dec. Anal. Calcd. for C17H16N2O2 HCl H2O: C, 60.98, H, 5.12; N, 8.37. Found: C, 60.78; H, 5.12; N, 8.45. Mass Spectrum: (EI; M+) m/z 280..1H-NMR (DMSO-d6; 400 MHz) δ15.2 (broad s, 1H), 8.18-8.2 (d, 1H), 7.76-7.8 (m, 2H), 7.45-7.54 (m, 2H), 7.32 (d 1H), 7.2-7.3 (m, 3H), 7.08-7.12 (d, 1H), 3.83 (s, 3H), 3.86 ppm (s, 3H).

Workup

  1. concentrationThe methanol solution was concentrated to dryness
  2. customThe residue was recrystallized from MeOH-Diethyl Ether

Sources & evidence

ORD record
ord-cb43e4461c64430ea50f9194c7340d9a
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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