Water → Acetanilide, 2-bromo-N-methyl-

HRID 2192364Notes

Reaction equation

HRID 2192364 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[Br:15][CH2:16][C:17](Br)=[O:18].O>ClCCl>[Br:15][CH2:16][C:17]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromide

Product 1

HCID 34495Acetanilide, 2-bromo-N-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-methyl aniline (5 mL) and potassium carbonate (9.6 g) in 100 mL dichloromethane was added bromoacetyl bromide (8.1 mL) (exotherm). The mixture was stirred for 4.5h then water was added. The phases were separated and the organic layer was concentrated. The crude product was purified by silica gel chromatography eluting with 0-100% EtOAc/cyclohexane. The relevant fractions were combined and evaporated and the residue was taken up in dichloromethane and washed with water. The organic layer was stirred with another portion of water for a few minutes and then the layers were separated. Evaporation of the organic layer gave the sub-titled compound (10.2 g) as a straw coloured solid.

Workup

  1. customThe phases were separated
  2. concentrationthe organic layer was concentrated
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with 0-100% EtOAc/cyclohexane
  5. customevaporated
  6. washwashed with water
  7. customthe layers were separated
  8. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-5872088bc0a441e9ad9dacb7f454debf
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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