Acetyl chloride → N-(1-methyl-1-phenylethyl)acetamide

HRID 2260565Notes

Reaction equation

HRID 2260565 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:6][C:5]([NH:14][C:1](=[O:3])[CH3:2])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 68509Cumylamine

Product 1

HCID 10749810N-(1-methyl-1-phenylethyl)acetamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetyl chloride (62 g) was dropwise added to a solution (1 l) of cumylamine (90 g) and a 48% aqueous solution of sodium hydroxide (70 ml) in toluene under ice-cooling and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the mixture was neutralized with a saturated aqueous solution of potassium carbonate and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was distilled away under reduced pressure to give 102.3 g of N-(1-methyl-1-phenylethyl)acetamide.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-d3ceca01eb3a4569a2100843ff68ce52
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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