Dimethylcarbamoyl Chloride → 6-(1,3-Oxazol-5-yl)-2-pyridinecarbonitrile

HRID 499454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499454
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=2[O-])=[CH:4][N:3]=[CH:2]1.C[Si]([C:17]#[N:18])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[O:1]1[C:5]([C:6]2[N:7]=[C:8]([C:17]#[N:18])[CH:9]=[CH:10][CH:11]=2)=[CH:4][N:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 597502552-(1,3-Oxazol-5-yl)pyridine N-oxide

Produkt 1

HCID 229395296-(1,3-Oxazol-5-yl)-2-pyridinecarbonitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6587NitroethaneLösungsmittel

Versuchsvorschrift

2-(1,3-Oxazol-5-yl)pyridine N-oxide (1.0 g, 6.6 mmol) was dissolved in nitroethane (15 ml), and trimethylsilyl cyanide (2.7 g, 27.2 mmol) and N,N-dimethylcarbamoyl chloride (3.0 g, 27.8 mmol) were added thereto. The mixture was stirred at room temperature for 5 days. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (1:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.84 g, 75%).

Aufarbeitung

  1. customThe solvent was evaporated
  2. washThe fractions eluted with ethyl acetate-hexane (1:1
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customrecrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4b6bf7ff28374454b25292fd4ebf1596
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767665B2

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