Acetic Anhydride → N-(3-Methylphenyl)acetamide

HRID 974408Notes

Reaction equation

HRID 974408 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1>C(O)(=O)C>[CH3:15][C:11]1[CH:10]=[C:9]([NH:8][C:5](=[O:7])[CH3:6])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 7934m-Toluidine2×

Product 1

HCID 10843N-(3-Methylphenyl)acetamideYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 11.2 grams (g) (0.11 mole) of acetic anhydride in 100 milliliters (mL) of acetic acid, was added 10.7 g (0.1 mole) of m-toluidine. The solution exothermed to 35° C. and, ten minutes (min) after all the m-toluidine was added, the product solution was concentrated in vacuo. The residue was taken up in EtOAc and was washed with H2O. The organic layer was dried over MgSO4 and concentrated in vacuo to give 14.46 g (97%) of product as a white powder (m.p. 65°-66° C). 1H NMR (CDCl3) 8:9.2 (1H, s, NH), 7.2 (2H, d, 8 Hz, aromatic), 7.0 (1H, t, 8 Hz, aromatic), 6.7 (1H, d, 8.0 Hz, aromatic).

Workup

  1. waitThe solution exothermed to 35° C. and, ten minutes
  2. concentrationthe product solution was concentrated in vacuo
  3. washwas washed with H2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f21066c30ee24d4ebb54a8ef50ec3d8e
Source dataset
uspto-grants-1991_11
Patent number
US05068392

Reaction notes

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