Dimethylcarbamoyl Chloride → 4-Phenyl-2-pyridinecarbonitrile

HRID 748202

Reaktionsgleichung

Reaktionsgleichung von HRID 748202
[C:1]1([C:7]2[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:18]#[N:19])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:18]([C:11]1[CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9][N:10]=1)#[N:19]

Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 708034-Phenylpyridine-1-oxideHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 877584-Phenyl-2-pyridinecarbonitrileAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6587NitroethaneLösungsmittel

Versuchsvorschrift

4-Phenylpyridine N-oxide (3.13 g, 18.3 mmol) was dissolved in nitroethane (30 ml), and trimethylsilyl cyanide (2.0 g, 20.2 mmol) and N,N-dimethylcarbamoyl chloride (1.7 ml, 18.5 mmol) were added thereto. The reaction mixture was stirred at room temperature for 45 hrs, concentrated under reduced pressure, combined with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure. The obtained crystals were collected by filtration, washed with diisopropyl ether and dried to give the titled compound (2.87 g, 89%). 1H-NMR (CDCl3) δ: 7.47-7.65 (5H, m), 7.72 (1H, dd, J=1.8, 5.2 Hz), 7.91 (1H, s), 8.75 (1H, d, J=5.1 Hz).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationThe obtained crystals were collected by filtration
  7. washwashed with diisopropyl ether
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2ec9959ab59a43ab848acc2abd8110f7
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399759B2

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