Acetic Anhydride → N-(4-Ethylphenyl)acetamide

HRID 1773540Notes

Reaction equation

HRID 1773540 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH2:8]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[CH3:9]>N1C=CC=CC=1>[CH2:8]([C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:5](=[O:7])[CH3:6])=[CH:12][CH:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 115044-Ethylaniline

Product 1

HCID 72893N-(4-Ethylphenyl)acetamideYield 101.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (4.3 mL, 45.45 mmol) was added to a mixture of 4-ethylaniline (5.0 g, 41.32 mmol) and pyridine (20 mL) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between dichloromethane and an aqueous solution of hydrochloric acid. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 6.857 g of N-(4-ethyl-phenyl)-acetamide as a brown solid without further purifications.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1f90d677736f4c55903eb79f9b476d3a
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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