Formamide → 4-(Oxazol-4-yl)benzonitrile

HRID 1436439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436439
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[CH:13]([NH2:15])=[O:14]>O>[O:14]1[CH:2]=[C:3]([C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[N:15]=[CH:13]1

Komponenten

4

Edukt 2

HCID 713FormamideHCID 986544-(Bromoacetyl)benzonitrile

Produkt 1

HCID 223795804-(Oxazol-4-yl)benzonitrileAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

4-(2-Bromo-acetyl)-benzonitrile (1.2 g, 5.4 mmol) was dissolved in formamide (10 mL) and heated to 110° C. for 72 h. The mixture was cooled, diluted with water and extracted five times with methylene chloride. The organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (5%-10% acetone in hexane) afforded 4-(1,3-oxazol-4-yl)benzonitrile (0.16 g, 17%) as a white solid. Analytical HPLC: purity 100% at 270 nm, 6.8 min; 100% at 210-370 nm, 6.8 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted five times with methylene chloride
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ac8d02057f434e9dad91f92bbdd277bd
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618990B2

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