Phenylacetyl chloride → N-(4-bromophenyl)-2-phenylacetamide

HRID 1478513Notes

Reaction equation

HRID 1478513 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:23](=[O:24])[CH2:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 78074-BromoanilineHCID 8471Triethylamine

Product 1

HCID 344475N-(4-bromophenyl)-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 250-mL round-bottom flask were placed a solution of 4-bromoaniline (17.1 g, 99.42 mmol) and triethylamine (30 g, 297 mmol) in dichloromethane (100 mL). Then, 2-phenylacetyl chloride (18.6 g, 120 mmol) was added dropwise with stirring, and the resulting solution was stirred at room temperature for 6 hours. The solids were filtered out, and the filtrate was concentrated under vacuum. The crude product was purified by re-crystallization from ethyl acetate to provide the title compound as a white solid.

Workup

  1. customInto a 250-mL round-bottom flask were placed
  2. stirringthe resulting solution was stirred at room temperature for 6 hours
  3. filtrationThe solids were filtered out
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crude product was purified by re-crystallization from ethyl acetate

Sources & evidence

ORD record
ord-d4e6715f3ff842009951e30083b9a0e8
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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