3,4-Dimethylaniline → 3',4'-Dimethylacetanilide

HRID 2054448Notes

Reaction equation

HRID 2054448 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH3:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[CH3:16])[NH2:12]>N1C=CC=CC=1>[CH3:8][C:9]1[CH:10]=[C:11]([NH:12][C:5](=[O:7])[CH3:6])[CH:13]=[CH:14][C:15]=1[CH3:16]

Participants

4

Reactant 2

HCID 72483,4-DimethylanilineHCID 7918Acetic Anhydride

Product 1

HCID 751443',4'-Dimethylacetanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Acetic anhydride (38.9 mL, 412 mmol) was added to a stirred solution of 3,4-dimethylaniline 1-5 (10.0 g, 82.5 mmol) in pyridine (150 mL) at ambient temperature. After stirring at approximately 60° C. for 2 h, the volatiles were removed in vacuo, and the residue was partitioned between diethyl ether and aqueous 1 N hydrochloric acid. The organic phase was separated and washed with saturated aqueous sodium bicarbonate, brine, dried (sodium sulfate) and concentrated in vacuo to afford 1-6 as a white crystalline solid.

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe residue was partitioned between diethyl ether and aqueous 1 N hydrochloric acid
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9cdc30c03d2e4d2681895fa7a66d369b
Source dataset
uspto-grants-2008_02
Patent number
US07329673B2

Reaction notes

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