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

HRID 640198

Reaktionsgleichung

Reaktionsgleichung von HRID 640198
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 231303655-p-Tolyloxy-thiophene-2-carbonitrileAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-824f8ec7affb46d39e8a0f939623bda5
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691882B2

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