N-Methylaniline → N-Methylacetanilide

HRID 641914

Reaction equation

HRID 641914 reaction equation
O([C:5]([CH3:7])=[O:6])C(C)=O.[CH3:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:8][N:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5](=[O:6])[CH3:7]

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 7918Acetic Anhydride

Product 1

HCID 11364N-MethylacetanilideYield 73.7%

Procedure

(CH3CO)2O (50 g, 480.77 mmol) was added to N-methylbenzenamine (10.7 g, 100.00 mmol), and the resulting solution was stirred at room temperature for 15 hours. The reaction mixture was then quenched by adding 200 mL of iced water. The resulting solution was extracted with dichloromethane (2×100 mL), and the organic layers were combined and concentrated to afford 11 g (70%) of N-methyl-N-phenylacetamide as a white solid.

Workup

  1. customThe reaction mixture was then quenched
  2. additionby adding 200 mL of iced water
  3. extractionThe resulting solution was extracted with dichloromethane (2×100 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ca8bdbb9d5d249b892e411cd95f5d6d2
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Linked notes

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