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

HRID 2226033Notes

Reaction equation

HRID 2226033 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 3,5-dimethylaniline 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-8eb1d653ad0a4504b41f519b48fc80d9
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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