4-Chloroaniline → Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-

HRID 1863987Notes

Reaction equation

HRID 1863987 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>C(#N)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 182511Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloroaniline (10.0 g) and triethylamine (16.4 ml) in acetonitrile (80 ml) was added dropwise pivaloyl chloride (14.5 ml) under ice-cooling. The mixture was allowed to warm to room temperature and stirred for 5 hrs. The obtained reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate (1500 ml) and water (1500 ml). The organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diethyl ether and hexane to give N-(4-chlorophenyl)-2,2-dimethylpropionamide (15.0 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. customThe obtained reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (1500 ml) and water (1500 ml)
  5. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from diethyl ether and hexane

Sources & evidence

ORD record
ord-a95436b355094fd3ac8346666989d318
Source dataset
uspto-grants-2009_12
Patent number
US07625887B2

Reaction notes

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