Water → 2-(1,3-Diphenyl-1H-1,2,4-triazol-5-yl)acetonitrile

HRID 1621152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621152
Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1.[C-:20]#[N:21].[K+].O>CS(C)=O>[C:8]1([N:7]2[C:3]([CH2:2][C:20]#[N:21])=[N:4][C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 9032Potassium CyanideHCID 866774905-(Bromomethyl)-1,3-diphenyl-1H-1,2,4-triazole

Produkt 1

HCID 131177802-(1,3-Diphenyl-1H-1,2,4-triazol-5-yl)acetonitrileAusbeute 114,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 5-(bromomethyl)-1,3-diphenyl-1H-1,2,4-triazole (265 mg, 843 μmol) and potassium cyanide (62.3 mg, 928 μmol) in DMSO (5 mL) was heated at 60° C. for 1.5 h. The reaction mixture was cooled to RT, poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The organic phases were washed with water (2×25 mL) and brine (1×25 mL), and the combined organic layer was dried over MgSO4 and concentrated in vacuo to give 251 mg of crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light yellow waxy solid (120 mg, 461 μmol, 54.7%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe organic phases were washed with water (2×25 mL) and brine (1×25 mL)
  4. dry with materialthe combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e3262c180684443d9049f7f3ab1c54a5
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772510B2

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