P-Cresol → 5-p-Tolyloxy-thiophene-2-carbonitrile

HRID 1693870Notes

Reaction equation

HRID 1693870 reaction equation
[N+]([C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1)([O-])=O.[CH:11]1[C:16]([OH:17])=[CH:15][CH:14]=[C:13]([CH3:18])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:13]1([CH3:18])[CH:12]=[CH:11][C:16]([O:17][C:4]2[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

Product 1

HCID 231303655-p-Tolyloxy-thiophene-2-carbonitrileYield 78.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophenecarbonitrile (6.30 g, 40.9 mmol) were added p-cresol (8.85 g, 81.8 mmol) and potassium carbonate (11.3 g, 81.8 mmol) under nitrogen atmosphere, which was stirred for 5 hours at 60° C. The reaction solution was cooled to room temperature, and extracted with ethyl acetate after addition of water. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1) to obtain the title compound (6.95 g, 78.9%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. additionafter addition of water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1)

Sources & evidence

ORD record
ord-db687cda6cf74259b7c6a0e64df5537e
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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