Dimethylcarbamoyl Chloride → 4-Pentyl-2-cyanopyridine

HRID 1269109

Reaktionsgleichung

Reaktionsgleichung von HRID 1269109
C[Si]([C:5]#[N:6])(C)C.[CH2:7](OC1C=C[N+]([O-])=CC=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:22][N:23]([CH3:27])C(Cl)=O.[C:28](=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:11]([C:10]1[CH:9]=[CH:27][N:23]=[C:22]([C:5]#[N:6])[CH:28]=1)[CH2:12][CH2:13][CH2:8][CH3:7]

Komponenten

6

Edukt 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 2958714-(Benzyloxy)pyridine N-oxideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 210760834-Pentyl-2-cyanopyridineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To trimethylsilyl cyanide (5.2 g, 52 mmol), 4-benzyloxy-pyridine 1-oxide (8.8 g, 44 mmol) in DCM (20 mL) was added, followed by dimethylcarbamoyl chloride (5.6 g, 52 mmol) in DCM (10 mL), dropwise, stirred at room temperature overnight. Sodium bicarbonate (100 mL, 10%) was added, stirred for 10 minutes and extracted twice with DCM (50 mL). The combined organic layer was dried over magnesium sulfate, solvent was removed to obtain the product, compound 10a (R9=Benzyloxy) (10.5 g, 100%).

Aufarbeitung

  1. stirringstirred for 10 minutes
  2. extractionextracted twice with DCM (50 mL)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate, solvent
  4. customwas removed

Quellen und Nachweise

ORD-Eintrag
ord-070d184ae5474511bc28b7bd985ae504
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199105B2

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