Acetic Anhydride → N-(1-phenylethyl)acetamide

HRID 2260562Notes

Reaction equation

HRID 2260562 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8]1([C@H:14]([NH2:16])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)(Cl)Cl>[C:8]1([CH:14]([NH:16][C:5](=[O:7])[CH3:6])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 222023N-(1-phenylethyl)acetamideYield 79.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetic anhydride (38.4 g) was dropwise added to a solution (200 ml) of (R)-(+)-1-phenylethylamine (30 g) in chloroform under ice-cooling. After completion of the reaction, ice water was added thereto and the mixture was extracted with chloroform. The extract was washed with 1N aqueous solution of sodium hydroxide and water. After drying, the mixture was concentrated under reduced pressure to give crystals, which were recrystallized from isopropyl ether to give 32.2 g of (+)-N-(1-phenylethyl)acetamide. [α]D =+143.5° (ethanol, c=1)

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with 1N aqueous solution of sodium hydroxide and water
  5. customAfter drying
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customto give crystals, which
  8. customwere recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-61c69d9af99a4c67abdf9238118a2817
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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