Acetic Anhydride → Acetamide, N-(3-methoxyphenyl)-

HRID 1593248Notes

Reaction equation

HRID 1593248 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 108243-Methoxyaniline

Product 1

HCID 11494Acetamide, N-(3-methoxyphenyl)-Yield 99.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

m-Anisidine (50 g, 0.406 mol) was added to acetic acid (25 mL)and cooled in an ice bath. Acetic anhydride (45.6 g, 0.447 mol) was added dropwise with stirring over 10 min. The resulting mixture was stirred and allowed to come to room temperature. After 1.5 hr the mixture was concentrated under reduced pressure until crystallization commenced. The crystals were collected and allowed to air dry in the hood overnight and finally in a desiccator to afford 66.5 g (99%) of N-(3-methoxyphenyl)acetamide.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe resulting mixture was stirred
  3. customto come to room temperature
  4. concentrationAfter 1.5 hr the mixture was concentrated under reduced pressure until crystallization
  5. customThe crystals were collected
  6. customto air dry in the hood overnight and finally in a desiccator

Sources & evidence

ORD record
ord-ec61b4a5064a44788b2458ee2ce27cbd
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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