4'-Bromoacetanilide → 1-(4-Bromophenyl)-2-methylbenzimidazole

HRID 1028380Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=O)[CH3:20])=[CH:14][CH:13]=1>>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N:8]=[C:19]2[CH3:20])=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 76834'-Bromoacetanilide

HCID 69115o-Iodonitrobenzene

Product 1

HCID 152631321-(4-Bromophenyl)-2-methylbenzimidazoleYield 76%

Procedure

The title compound was prepared with the analogous procedure described in example 1 using 1-Iodo-2-nitrobenzene (124 mg, 0.5 mmol) and N-(4-bromophenyl)-acetamide (128 mg, 0.6 mmol) as starting materials to yield the title compound as a yellow solid (109 mg, 76%). 1H NMR (DMSO) δ 2.63 (s, 3 H), 7.34 (d, J=7.9 Hz, 1H), 7.41 (t, J=7.9 Hz, 1 H), 7.48 (t, J=7.9 Hz, 1 H), 7.64 (d, J=8.6 Hz, 2 H), 7.82 (d, J=7.9 Hz, 1 H), 7.92 (d, J=8.6 Hz, 2 H); 13C NMR δ 12.8, 111.7, 115.4, 123.6, 125.1, 125.2, 129.3, 132.5, 133.3, 134.5, 152.8, 157.6.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-d21220320bce4cbdbb6e261dbee68822
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

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