Water → (S)-N-(1-phenylethyl)acetamide

HRID 1282195Notes

Reaction equation

HRID 1282195 reaction equation
[C:1]1([C@@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18].O>ClC(Cl)C>[C:1]1([C@@H:7]([NH:9][C:17](=[O:19])[CH3:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 758181-Phenethylamine, (-)-

Product 1

HCID 737096(S)-N-(1-phenylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (S)-(−)-1-phenylethylamine (121 g) and triethylamine (168 ml) in dichloroethane (1200 ml) was added dropwise acetyl chloride (78.2 ml) over 1 hr under ice-cooling and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water (1000 ml) and the organic layer was separated. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound (143.4 g) as pale-yellow crystals, m.p.=99-101° C.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c810d251722f43a1be77e7b53d809632
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

Loading…