Water → 3-bromo-N-ethylbenzamide

HRID 1059201Notes

Reaction equation

HRID 1059201 reaction equation
[OH-].[Na+].O.Cl.[CH2:5]([NH2:7])[CH3:6].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](Cl)=[O:13]>CO>[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:7][CH2:5][CH3:6])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 41602713-bromo-N-ethylbenzamideYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium hydroxide (3.80 g) in methanol (50 ml)—water (15 ml) was added by portions ethylamine hydrochloride (7.80 g) at 0° C. and the mixture was stirred for 5 min. 3-Bromobenzoyl chloride (5.53 g) was added dropwise and the mixture was stirrd at room temperature for 1 h. Methanol was evaporated under reduced pressure, and ethyl acetate was added to the residue for partitioning. 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 (5.47 g) as colorless powder crystals.

Workup

  1. waitthe mixture was stirrd at room temperature for 1 h
  2. customMethanol was evaporated under reduced pressure, and ethyl acetate
  3. additionwas added to the residue
  4. customfor partitioning
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-d6a294882369475ca6cee65d6547307f
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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