Acetanilide → 5-Chloro-2-methyl-1-phenyl-1H-benzimidazole

HRID 1028367Notes

Reaction equation

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

Participants

Reactant 2

HCID 904Acetanilide

HCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 970245-Chloro-2-methyl-1-phenyl-1H-benzimidazoleYield 56%

Procedure

The title compound was prepared with the analogous procedure described in example 1 using 4-Chloro-1-bromo-2-nitrobenzene (118 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol), as starting materials to yield the title compound as yellow solid (68 mg, 56% yield). mp 109-111° C. 1H NMR (DMSO) δ 2.52 (s, 3 H), 7.22 (d, J=8.6 Hz, 1 H), 7.34 (d, J=8.6 Hz, 1 H), 7.48-7.59 (m, 5 H), 7.86 (s, 1 H); 13C NMR δ 13.5, 112.2, 116.4, 123.9, 126.9, 127.9, 129.7, 130.1, 133.9, 138.5, 154.0, 157.0. HRMS (FAB): cal. for C14H12N2Cl [M+H+]: 243.0689; found: 243.0684.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-f083874f4bee455b9b9250c464cb5c95
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

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