Acetic Acid → Acetanilide

HRID 1733651Notes

Reaction equation

HRID 1733651 reaction equation
[C:1]([OH:4])(=O)[CH3:2].C(N(CC)CC)C.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CS(ON1C2C=CC=CC=2N=N1)(=O)=O>C(OCC)(=O)C>[C:1]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 8471TriethylamineHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 904AcetanilideYield 103.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.3 g), triethylamine (0.7 ml) and aniline (0.5 g) are dissolved in ethyl acetate (10 ml), and thereto is added 1-methanesulfonyloxy-1,2,3-benzotriazole (1.05 g), and the mixture is stirred at room temperature for 1 hour. After allowing to stand overnight, the reaction mixture is extracted with ethyl acetate. The extract is washed with water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off to give acetanilide (0.7 g). The product recrystallized from water has a melting point of 110°-112° C.

Workup

  1. waitto stand overnight
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter drying
  6. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-ac7d2d7aa69741e5940029955082c499
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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