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

HRID 1597554Notes

Reaction equation

HRID 1597554 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-fbab596cac314053b00c408385e9a1b0
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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