Acetanilide → N-Phenyl-N-(thiophen-2-yl)acetamide

HRID 1977653Notes

Reaction equation

HRID 1977653 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].I[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>[Cu](I)I.C(OCC)(=O)C>[S:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[N:4]([C:1](=[O:3])[CH3:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 904AcetanilideHCID 962WaterHCID 11430Potassium CarbonateHCID 189212-Iodothiophene

Product 1

HCID 29540N-Phenyl-N-(thiophen-2-yl)acetamideYield 18.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of acetanilide (6.0 g), 2-iodothiophene (18.6 g), copper iodide (864 mg), and potassium carbonate (12.2 g) was heated for 2 hours at 150° C. After the mixture was allowed to cool, water and ethyl acetate were added thereto. The resulting mixture was stirred, then filtered with celite. The aqueous phase was extracted. The organic phase was washed with water and saturated brine, and dried over sodium sulfate. The resulting solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, ethyl acetate:hexane=1:5) to obtain N-(2-thienyl)acetanilide (1.77 g; yield, 18%) as a light brown solid.

Workup

  1. temperatureto cool
  2. filtrationfiltered with celite
  3. extractionThe aqueous phase was extracted
  4. washThe organic phase was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe resulting solution was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (developing solvent, ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-2c5ae1572ed34c839016b30d59bf0e63
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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