Acetyl chloride → N-(2-tert-butylphenyl)acetamide

HRID 534830Notes

Reaction equation

HRID 534830 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>C1COCC1>[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH:7][C:19](=[O:21])[CH3:20])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 805742-tert-Butylaniline

Product 1

HCID 343805N-(2-tert-butylphenyl)acetamideYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-tert-butylaniline (5.0 g, 33.5 mmol) and triethylamine (11.2 g, 110.6 mmol) in THF (350 mL) was added acetyl chloride (2.89 g, 36.9 mmol). After being stirred at room temperature for 3 h, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting white solid was triturated with hexane/ethyl acetate to give the title compound (6.13 g) as a white crystalline powder.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting white solid was triturated with hexane/ethyl acetate

Sources & evidence

ORD record
ord-caa101ae1e0b48a99cf2072b2995831c
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…