Water → N-(3-bromophenyl)propanamide

HRID 1059193Notes

Reaction equation

HRID 1059193 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[C:16](Cl)(=[O:19])[CH2:17][CH3:18].O>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:16](=[O:19])[CH2:17][CH3:18])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 115623-BromoanilineHCID 62324Propionyl chloride

Product 1

HCID 806279N-(3-bromophenyl)propanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromoaniline (5.10 g) and triethylamine (8.3 ml) in THF (40 ml) was added dropwise propionyl chloride (2.8 ml) at 0° C. and the mixture was stirred at 0° C. for 2 h. Water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The organic layer was washed with water and brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the title compound (5.60 g) as colorless needle crystals.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8cc7f53c99ea4d8fb0ab111d9f8626a4
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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