Phenylacetyl chloride → N-(4-methylphenyl)-2-phenylacetamide

HRID 1357769Notes

Reaction equation

HRID 1357769 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]1([CH2:15][C:16](Cl)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:16](=[O:17])[CH2:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 7813p-ToluidineHCID 516892Sodium Bicarbonate

Product 1

HCID 854300N-(4-methylphenyl)-2-phenylacetamideYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.0 g (9.3 mmol) of 4-methylaniline is dissolved in toluene (10 ml) at 0° C., under a nitrogen atmosphere. A solution of phenylacetyl chloride (1.25 ml, 9.4 mmol) in 20 ml of toluene is added dropwise to the medium. The reaction mixture is stirred at room temperature for 2 h and the medium is then hydrolyzed with cold sodium hydrogen carbonate solution. The two-phase system is stirred vigorously for 30 min and the organic phase is then collected. The aqueous phase is extracted with ethyl acetate (twice). The organic phase is dried over MgSO4 and then evaporated. The residue obtained is purified by chromatography on a column of silica (3/7 EtOAc/PE) to give 1.9 g (92%) of compound 47.

Workup

  1. stirringThe two-phase system is stirred vigorously for 30 min
  2. customthe organic phase is then collected
  3. extractionThe aqueous phase is extracted with ethyl acetate (twice)
  4. dry with materialThe organic phase is dried over MgSO4
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica (3/7 EtOAc/PE)

Sources & evidence

ORD record
ord-369fc4bac03a4c5b91b7239c55a914fe
Source dataset
uspto-grants-2003_07
Patent number
US06593342B1

Reaction notes

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