Chloroacetyl chloride → N-(4-Bromophenyl)-2-chloroacetamide

HRID 1387050Notes

Reaction equation

HRID 1387050 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>CC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:17](=[O:18])[CH2:16][Cl:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 78074-BromoanilineHCID 10340Sodium Carbonate

Product 1

HCID 17374N-(4-Bromophenyl)-2-chloroacetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8.60 g (0.05 mol) of 4-bromoaniline, 10.60 g (0.10 mol) of Na2CO3, and 6.78 g (0.06 mol) of chloroacetyl chloride in 100 mL of acetone was stirred at ambient temperature for 3 h. The mixture was concentrated in vacuo, and the residue was partitioned between EtOAc and H2O. The organic layer was separated, washed with H2O, dried over Na2SO4, filtered, and evaporated in vacuo to give 11.4 g of analytically pure title compound as light crystals.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and H2O
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-df4843024a11476e8e802ccbf97a89a0
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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