4-Nitro-1,2-phenylenediamine → 2-[2-(3,4-Dimethoxy-phenyl)-vinyl]-5-nitro-1H-benzimidazole

HRID 1278726Notes

Reaction equation

HRID 1278726 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].Cl.CO[C:15](=N)[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1>CO>[CH3:27][O:26][C:20]1[CH:19]=[C:18](/[CH:17]=[CH:16]/[C:15]2[NH:10][C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[N:11]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 51117914-Nitro-1,2-phenylenediamineHCID 86758495Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride

Product 1

HCID 1784900102-[2-(3,4-Dimethoxy-phenyl)-vinyl]-5-nitro-1H-benzimidazoleYield 23.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-nitro-1,2-phenylenediamine (1.2 g; 8 mmol) and methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride (2.0 g; 8 mmol) in methanol (70 mL) was refluxed for 18 hours. Solution was concentrated to dryness. The residue was recrystallized from MeOH to obtain 603 mg (23% yield) of the title compound as a yellow solid, m.p. 223-225° C. Anal. Calcd. for C17H15N3O4: C, 62.76, H, 4.65; N, 12.92. Found: C, 62.67; H, 4.62; N, 13.05. Mass spectrum: (EI; M+) m/z 325. 1H-NMR (DMSO-d6; 400 MHz) δ13.2(broad s, 1H), 8.4 (broad s, 1H), 8.1(dd, 1H), 7.74 (s, 1H), 7.62-7.72 (m, 1H), 7.35 (d 1H), 7.19-7.23 (dd, 1H), 7.17 (s, 1H), 7.0 (d,1H),3.85 (s, 3H), 3.8 ppm (s, 3H).

Workup

  1. temperaturewas refluxed for 18 hours
  2. concentrationSolution was concentrated to dryness
  3. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-b2c1ffea94dd40a2b898d59c6871bf37
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

Loading…