Acetic Acid → Acetanilide

HRID 1733650Notes

Reaction equation

HRID 1733650 reaction equation
[C:1]([OH:4])(=O)[CH3:2].C(N(CC)CC)C.CS(ON=C(C#N)C(OCC)=O)(=O)=O.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C>[C:1]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 8471TriethylamineHCID 54531055Ethyl cyano{[(methanesulfonyl)oxy]imino}acetate

Product 1

HCID 904AcetanilideYield 88.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.3 g) and triethylamine (0.7 ml) are dissolved in ethyl acetate (10 ml), and thereto is added ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (1.1 g) and the mixture is stirred for 40 minutes. To the solution is added aniline (0.5 g) and the mixture is stirred for 2 hours. The reaction mixture is washed well with 1 N aqueous sodium hydrogen carbonate, water and 1 N hydrochloric acid in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off to give flasks of acetanilide (0.6 g), melting poit: 95°-105° C. The product recrystallized from water has a melting point of 104°-108° C.

Workup

  1. stirringthe mixture is stirred for 2 hours
  2. washThe reaction mixture is washed well with 1 N aqueous sodium hydrogen carbonate, water and 1 N hydrochloric acid in order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter drying
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-1923f6e20589497eb2f8ad3f6c2a8f66
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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