Acetic Anhydride → Acetamide, N-(3,5-dimethylphenyl)-

HRID 2226608Notes

Reaction equation

HRID 2226608 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1(C)C=CC=CC=1>[C:10]([NH:5][C:4]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:2]([CH3:1])[CH:3]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 79493,5-Dimethylaniline

Product 1

HCID 74903Acetamide, N-(3,5-dimethylphenyl)-Yield 90.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 15.2 g (125 mmole) of 3,5dimethylaniline in 60 mL of toluene was added 15 g (146 mmole) of acetic anhydride, whereupon the internal temperature rose to 75° C. The mixture was allowed to cool to room temperature and the solvent was removed in vacuo. The residue was dissolved in 150 mL of hot ethyl acetate and the solution allowed to stand for 16 hours. The resulting mixture was cooled at 5° C. for 3 hours and the solid collected by filtration to give 18.43 g (90%) of off-white crystals.

Workup

  1. customrose to 75° C
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 150 mL of hot ethyl acetate
  4. temperatureThe resulting mixture was cooled at 5° C. for 3 hours
  5. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-156114ff7e9948188cdc16f103c87718
Source dataset
uspto-grants-1994_09
Patent number
US05348955

Reaction notes

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