4-Bromoaniline → N-(4-bromophenyl)-4-chloro-3-nitrobenzamide

HRID 2197784Notes

Reaction equation

HRID 2197784 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:15])[C:13]2[CH:17]=[CH:18][C:10]([Cl:9])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 81531DiisopropylethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromoaniline (2.58 g 14.99 mmol) in dry CH2Cl2 (100 mL) was treated with 4-chloro-3-nitrobenzoyl chloride (3.60 g, 17.99 mmol) and N,N-diisopropyl-ethylamine (3.14 mL, 17.99 mmol), and the resulting mixture stirred at room temperature for 17 hours. The solvent was concentrated under vacuum giving the title compound and the residue taken up in ethyl acetate (100 mL) and washed with water and brine. The organic extract was dried over Na2SO4, filtered and concentrated under vacuum giving the title compound as a tan solid (5.132 g, 14.45 mmol, 96%).

Workup

  1. concentrationThe solvent was concentrated under vacuum

Sources & evidence

ORD record
ord-fb390fc8fc774d83919bc139d22bbc03
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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