2,3-Dimethyl-5,6-diamino-1,4-dimethoxybenzene → 2-[2-(3,4-Dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-1H-benzoimidazole

HRID 1278723Notes

Reaction equation

HRID 1278723 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[C:5]([NH2:11])=[C:4]([NH2:12])[C:3]=1[O:13][CH3:14].Cl.CO[C:18](=N)[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1>CO>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([CH:20]=[CH:19][C:18]2[NH:12][C:4]3[C:3]([O:13][CH3:14])=[C:2]([CH3:1])[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[C:5]=3[N:11]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 184311722,3-Dimethyl-5,6-diamino-1,4-dimethoxybenzeneHCID 86758495Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride

Product 1

HCID 540257852-[2-(3,4-Dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-1H-benzoimidazoleYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,3-dimethyl-5,6-diamino-1,4-dimethoxybenzene (2.57 g; 10 mmol) and methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride (1.96 g; 10 mmol) in methanol (35 mL) was stirred at ambient temperature for 18 hours. The methanol solution was concentrated to 15 mL. The yellow precipitate was separated by filtration. Recrystallization from MeOH afforded 2.1 g (58% yield) of the title compound as yellow solid, m.p. 116-119° C. Anal. Calcd. for C21H24N2O4: C, 66.46, H, 6.57; N, 7.60. Found: C, 66.83; H, 6.64; N, 7.41. Mass spectrum: (EI,M+) m/z 368 1H-NMR (DMSO-d6; 400 MHz) δ12.4-12.5(broad s,1H), 7.6-7.4 (d, 1H), 7.2 (d, 1H), 7.07-7.16 (m, 2H), 7.0 (d, 1H), 3.84(s, 3H), 3.78 (s, 3H), 2.2 ppm (s, 3H).

Workup

  1. concentrationThe methanol solution was concentrated to 15 mL
  2. customThe yellow precipitate was separated by filtration
  3. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-2f6a074a9a434532b2bccddf882caf0c
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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