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

HRID 396806Notes

Reaction equation

HRID 396806 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]>C1COCC1>[CH3:11][C:10]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 108243-Methoxyaniline

Product 1

HCID 11494Acetamide, N-(3-methoxyphenyl)-Yield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of m-anisidine (12.3 g, 0.1 mol) in THF (80 mL) was added acetic anhydride (11.3 mL, 0.12 mol) at 0° C. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with water (50 mL), brine (30 mL), dried over MgSO4, and concentrated in vacuo. The resulting solid was recrystallized from methylene chloride-hexane to give the subtitle compound (15.9 g, 96.4% yield).

Workup

  1. washThe reaction mixture was washed with water (50 mL), brine (30 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-1f9facf764844d6084e545ef14107461
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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