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

HRID 1019090Notes

Reaction equation

HRID 1019090 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].C(N(CC)CC)C>C(Cl)Cl>[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

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 79493,5-DimethylanilineHCID 8471Triethylamine

Product 1

HCID 74903Acetamide, N-(3,5-dimethylphenyl)-Yield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,5dimethylaniline (20 g, 165 mmol), acetic anhydride (24 mL, 247 mmol) and triethylamine (70 mL, 495 mmol) in methylene chloride (300 mL is stirred at room temperature for 16 hours. The mixture is washed with water, dried (magnesium sulfate) and rotary evaporated. The residue is triturated with hexane and filtered to afford N-acetyl-3,5-dimethylaniline (25 g).

Workup

  1. washThe mixture is washed with water
  2. dry with materialdried (magnesium sulfate) and rotary evaporated
  3. customThe residue is triturated with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9fbb8e492b9f4a319ac0cb4d89057ff5
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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