Formanilide → 1-Phenyl-1H-benzoimidazole

HRID 1028386Notes

Reaction equation

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

Participants

Reactant 2

HCID 7671Formanilide

HCID 69115o-Iodonitrobenzene

Product 1

HCID 6066691-Phenyl-1H-benzoimidazoleYield 72.1%

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-Phenyl-formamide (73 mg, 0.6 mmol) as starting materials to yield the title compound as a yellow solid (70 mg, 72%). 1H NMR (DMSO) δ 7.28-7.33 (m, 2 H), 7.49 (d, J=7.3 Hz, 1 H), 7.59-7.68 (m, 5 H), 7.79 (d, J=6.9 Hz, 1 H), 8.56 (br s, 1 H); 13C NMR δ 110.6, 119.9, 122.4, 123.6, 123.9, 127.6, 130.0, 133.1, 135.9, 143.8.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-58bc9f1a65ed47a09d8654dfdd3f5d31
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

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