Acetanilide → HCID 25216871, compound

HRID 1028389Notes

Reaction equation

HRID 1028389 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1Br.[C:15]1([NH:21][C:22](=O)[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:1][O:2][C:3]([C:4]1[C:5]2[N:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:22]([CH3:23])=[N:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:14]

Participants

3

Reactant 2

HCID 904AcetanilideHCID 79263Methyl 2-bromo-3-nitrobenzoate

Product 1

HCID 25216871HCID 25216871, compoundYield 30%

Procedure

The title compound was prepared with the analogous procedure described in example 3 using 2-Bromo-3-nitrobenzoic acid methyl ester and N-phenylacetamide (81 mg, 0.6 mmol) as starting materials to yield the title compound as viscous oil (40 mg, 30%). 1H NMR (DMSO) δ 2.41 (s, 3 H), 3.08 (s, 3 H), 7.39-7.63 (m, 7 H), 7.96 (br s, 1 H); 13C NMR δ 14.1, 51.8, 117.2, 121.1, 123.0, 124.9, 137.0, 139.3, 139.6, 137.0, 140.2, 155.2, 165.7.

Workup

  1. customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record
ord-fe5fe0c00f314a2384bc116579ee30e6
Source dataset
uspto-grants-2014_05
Patent number
US08735586B2

Reaction notes

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