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

HRID 605049Notes

Reaction equation

HRID 605049 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-nitrobenzamideYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromoaniline (2.58 g 14.99 mmol) in dry methylene chloride (100 mL) was treated with 4-chloro-3-nitrobenzoyl chloride (3.60 g, 17.99 mmol) and N,N-diisopropylethylamine (3.14 mL, 17.99 mmol), and the resulting mixture stirred at room temperature for 17 hours. The solvent was removed by rotary evaporation in vacuo, the residue taken up in ethyl acetate (100 mL) and washed with water (2×50 mL) and brine. Dried the organic extract over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the product as a tan solid (5.132 g, 14.45 mmol, 96%)

Workup

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. washwashed with water (2×50 mL) and brine
  3. customDried the
  4. extractionorganic extract over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a7bcb35d0ee487b9a2bbce135169c17
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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