Phenylacetyl chloride → N-{2-[4-(Phenylacetyl)phenyl]propan-2-yl}acetamide

HRID 1678801Notes

Reaction equation

HRID 1678801 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:13])[CH3:12])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[C:14]1([CH2:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[CH3:3][C:2]([NH:10][C:11](=[O:13])[CH3:12])([C:4]1[CH:5]=[CH:6][C:7]([C:21](=[O:22])[CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:9]=1)[CH3:1]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10749810N-(1-methyl-1-phenylethyl)acetamide

Product 1

HCID 59472934N-{2-[4-(Phenylacetyl)phenyl]propan-2-yl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(1-methyl-1-phenylethyl)acetamide (21.3 g, 121 mmol), phenylacetyl chloride (19.5 g, 126 mmol) and aluminum trichloride (19 g, 142 mmol) in methylene chloride (140 mL) was stirred overnight at room temperature under an atmosphere of nitrogen. The reaction was poured onto ice and stirred until the ice melted, then the layers were separated and the organic layer was washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography gave the title compound. MS (M+H+): calculated=295.38, observed=296.1

Workup

  1. additionThe reaction was poured onto ice
  2. customthe layers were separated
  3. washthe organic layer was washed with saturated sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-df162f5ecc1c4217878c721dac8e9460
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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