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

HRID 497245Notes

Reaction equation

HRID 497245 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-7f531ebc8e804672899b8b905fb0920a
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

Loading…