Sodium Cyanide → 2-(Dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrile

HRID 1397399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397399
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]=O)[N:12]=2)=[CH:4][CH:3]=1.Cl.[CH3:16][NH:17][CH3:18].[C-:19]#[N:20].[Na+]>C1COCC1.CO.O>[CH3:16][N:17]([CH3:18])[CH:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH:10]=1)[C:19]#[N:20]

Komponenten

6

Edukt 3

HCID 8929Sodium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 218062352-(4-Fluoro-phenyl)-oxazole-4-carbaldehyde

Produkt 1

HCID 673252862-(Dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrileAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(4-Fluorophenyl)oxazole-4-carbaldehyde (1.0 g, 5.23 mmol) was dissolved in THF-MeOH (20 mL, 1:1 v/v). This solution was added to a solution of dimethylamine hydrochloride (470 mg, 5.7 mmol) and NaCN (640 mg, 13.0 mmol) in water. The resulting reaction mixture was stirred at room temperature for 2 h, and then diluted with water and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 2-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrile (1.0 g, crude) as a brown oil, which was used without further purification. MS (ESI) m/z: Calculated for C13H12FN3O: 245.10. found: 245.9 (M+H)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-01d021e1c29c4e0287e929b2644bd438
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901156B2

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