Acetic Anhydride → N-[4-(2-methylbutan-2-yl)phenyl]acetamide

HRID 1424235Notes

Reaction equation

HRID 1424235 reaction equation
[CH3:1][C:2]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[C:13](OC(=O)C)(=[O:15])[CH3:14]>C1COCC1>[CH3:5][C:2]([C:6]1[CH:7]=[CH:8][C:9]([NH:10][C:13](=[O:15])[CH3:14])=[CH:11][CH:12]=1)([CH3:1])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 221031Benzenamine, 4-(1,1-dimethylpropyl)-

Product 1

HCID 346190N-[4-(2-methylbutan-2-yl)phenyl]acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(1,1-dimethylpropyl)aniline (Preparation 100, 12.5 g, 0.076 mol) in THF (100 mL) was added acetic anhydride slowly at 0° C. The reaction was stirred at room temperature for 8 hours. The reaction was extracted with EtOAc, washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound (12 g, 76%).

Workup

  1. extractionThe reaction was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8970955483a24acbb771fce73ce04c61
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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