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

HRID 1994110Notes

Reaction equation

HRID 1994110 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:12](Cl)(=[O:14])[CH3:13]>C(Cl)Cl.O>[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH:7][C:12](=[O:14])[CH3:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 805742-tert-Butylaniline

Product 1

HCID 343805N-(2-tert-butylphenyl)acetamideYield 106.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-tert-butylaniline (2.0 g, 2.1 mL, 13.4 mmol) and TEA (2.8 mL, 20.1 mmol) in DCM (100 mL) was cooled to 0° C. Acetyl chloride (1.0 mL, 14.7 mmol) was added dropwise. The resulting solution was allowed to stir and warm to rt over 2 h. The reaction mixture was diluted with water and DCM. The organic phase was washed with 1N HCl and brine, dried over Na2SO4, filtered and concentrated to give the title compound as a white solid (2.73 g, >100%). 1H NMR (400 MHz, CDCl3) δ: 7.51-7.53 (m, 1H), 7.39-7.41 (m, 1H), 7.14-7.24 (m, 2H), 2.21 (s, 2.2H), 1.92 (s, 0.9H), and 1.41 (s, 9H).

Workup

  1. washThe organic phase was washed with 1N HCl and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b328207f86b4457e8daca074cfffe489
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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