Acetyl chloride → HCID 18423181, compound

HRID 2260566Notes

Reaction equation

HRID 2260566 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]([NH:14][C:15](=[O:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7].[C:18](Cl)(=[O:20])[CH3:19]>ClC(Cl)C>[C:18]([C:11]1[CH:10]=[CH:9][C:8]([C:6]([NH:14][C:15](=[O:17])[CH3:16])([CH3:5])[CH3:7])=[CH:13][CH:12]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10749810N-(1-methyl-1-phenylethyl)acetamide

Product 1

HCID 18423181HCID 18423181, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Aluminum chloride (41.5 g) was portionwise added to a solution (75 ml) of N-(1-methyl-1-phenylethyl)acetamide (25 g) and acetyl chloride (16.6 g) in dichloroethane under ice-cooling. The mixture was stirred at said temperature for 1 hour and then at 50°-60° C. for 1 hour. After completion of the reaction, the reaction mixture was poured into ice water and extracted with chloroform. The extract was washed with water, dried and concentrated under reduced pressure to give crystals which were then recrystallized from ethyl acetate-isopropyl ether to give 20.4 g of N-(1-(4-acetylphenyl)-1-methylethyl)acetamide.

Workup

  1. temperaturecooling
  2. customfor 1 hour
  3. customAfter completion of the reaction
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give crystals which
  9. customwere then recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-a5a1bba2bce64818b2e7422e8fcfc918
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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