Water → N-(4-Methoxyphenyl)Acetamide

HRID 2068700Notes

Reaction equation

HRID 2068700 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](Cl)(=[O:19])[CH3:18].O>C(Cl)Cl>[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

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 7732P-AnisidineHCID 8471Triethylamine

Product 1

HCID 5827N-(4-Methoxyphenyl)AcetamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of p-anisidine (25 g, 203.0 mmol) in DCM (300.0 mL) was added triethyl amine (90.0 mL, 609.0 mmol) dropwise and the reaction mixture was stirred at the same temperature for 15 min. Acetyl chloride (23.0 mL, 304.50 mmol) was then added and the reaction mixture was continued to stir at room temperature for 1 h. After the completion of the reaction (TLC monitoring), water (500 mL) was added and extracted with DCM (2×300 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product (30.0 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ 1.99 (s, 3H), 3.70 (s, 3H), 6.86 (d, J=8.80 Hz, 2H), 7.48 (d, J=8.80 Hz, 2H) and 9.77 (br s, 1H).

Workup

  1. stirringto stir at room temperature for 1 h
  2. additionwas added
  3. extractionextracted with DCM (2×300 mL)
  4. washThe combined organics was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61a51019c61247ba9aa867895f09b8e7
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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