Benzanilide → 1H-Benzimidazole, 1,2-diphenyl-

HRID 1028372Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:3]1([N:8]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:11]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

Reactant 2

HCID 7168Benzanilide

HCID 69115o-Iodonitrobenzene

Product 1

HCID 1376611H-Benzimidazole, 1,2-diphenyl-Yield 70.3%

Procedure

The title compound was prepared with the analogous procedure described in example 1 using 1-Iodo-2-nitrobenzene (125 mg, 0.5 mmol) and benzanilide (118 mg, 0.6 mmol) as starting materials to yield the title compound as pale yellow solid (95 mg, 70%). mp 105-107° C. 1H NMR (DMSO) δ 7.24 (d, J=7.9 Hz, 1 H), 7.35-7.62 (m, 12 H), 7.84 (d, J=7.6 Hz, 1 H); 13C NMR δ 111.0, 118.1, 123.7, 124.1, 127.5, 127.9, 128.4, 129.2, 129.3, 130.0, 130.2, 135.5, 136.2, 139.3, 151.3. HRMS (FAB): cal. for C19H15N2 [M+H+]: 271.1235; found: 271.1230.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-fe690af5aba64e9187d6cd3bfc4a2fe5
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

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