P-Anisidine → N-(4-Methoxyphenyl)Acetamide

HRID 1841370Notes

Reaction equation

HRID 1841370 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:17](=[O:19])[CH3:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 5827N-(4-Methoxyphenyl)AcetamideYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Paraanisidine (136.34 g, 1.108 mol) was dissolved in dichloromethane (500 ml), triethylamine (234 ml, 1.66 mol) and acetic anhydride (114.8 ml, 1.22 mol) were added thereto, and the resulting mixture was stirred for 1 hour. After completion of reaction, the reaction solution was concentrated. Water (800 ml) was added to the residue and the resulting mixture was stirred and filtered to give 168.0 g (1.16 mol, Yield 92%) of the title compound.

Workup

  1. customAfter completion of reaction
  2. concentrationthe reaction solution was concentrated
  3. additionWater (800 ml) was added to the residue
  4. stirringthe resulting mixture was stirred
  5. filtrationfiltered

Sources & evidence

ORD record
ord-cb09baf6b6cc4959be12e71f196601e2
Source dataset
uspto-grants-2004_01
Patent number
US06683095B2

Reaction notes

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