Acetanilide → 2,4-Dimethyl-1-phenyl-1H-benzimidazole

HRID 1931272Notes

Reaction equation

HRID 1931272 reaction equation
Cl[C:2]1[C:3]([N+:9]([O-])=O)=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[C:12]1([NH:18][C:19](=O)[CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:20][C:19]1[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=2[N:9]=1

Participants

3

Reactant 2

HCID 904AcetanilideHCID 793283-Chloro-2-nitrotoluene

Product 1

HCID 248214482,4-Dimethyl-1-phenyl-1H-benzimidazoleYield 33.3%

Procedure

Method A applied to 3-chloro-2-nitrotoluene (86 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) yielded the title compound as brown solid (37 mg, 33%). 1H NMR (DMSO) δ 2.46 (s, 3H), 2.55 (s, 3H), 6.88 (d, J=7.3Hz, 1H), 7.04-7.11 (m, 2H), 7.50-7.64 (m, 5H); 13C NMR δ 13.8, 16.3, 107.5, 122.5, 122.6, 126.8, 129.9, 135.1, 135.3, 150.3, 158.3.

Sources & evidence

ORD record
ord-0d7dfd91bbf14c6faf95f2a1bb47efb4
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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