Dimethylcarbamoyl Chloride → 4-Phenyl-2-pyridinecarbonitrile

HRID 2396757

Reaktionsgleichung

Reaktionsgleichung von HRID 2396757
[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.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[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

6

Edukt 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 708034-Phenylpyridine-1-oxideHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 877584-Phenyl-2-pyridinecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-phenylpyridine N-oxide (25 g, 0.146 mmol) in dichloromethane (200 ml) at room temperature was added trimethylsilyl cyanide (17.4 g), followed by the slow addition of dimethyl carbamyl chloride (16.2 ml) in dichloromethane (50 ml) over a 30 minute period. The reaction mixture was stirred at room temperature for one day, and then to it potassium carbonate solution (10%,150 ml) was added slowly. Stirring continued for an additional 30 minutes, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The extracts were combined and dried over magnesium sulfate. Evaporation in vacuo gave a crude reaction product (35 g) as a white solid. It was used without further purification.

Aufarbeitung

  1. stirringStirring
  2. waitcontinued for an additional 30 minutes
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation in vacuo
  7. customgave a crude
  8. customIt was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-f04bcee204ef4760aef8b2232e22f265
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05494919

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