Dimethylcarbamoyl Chloride → 4-Pentyl-2-cyanopyridine

HRID 1269098

Reaktionsgleichung

Reaktionsgleichung von HRID 1269098
CO[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](O)=O)[CH:4]=1.C[Si](C#N)(C)C.CO[C:20]1[CH:25]=[CH:24][N+]([O-])=[CH:22][CH:21]=1.C[N:28](C)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:22]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:28])[CH:4]=1)[CH2:21][CH2:20][CH2:25][CH3:24]

Komponenten

7

Edukt 5

HCID 6598Dimethylcarbamoyl ChlorideHCID 707434-Methoxypyridine N-oxideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 20500994-Methoxypyridine-2-carboxylic acid

Produkt 1

HCID 210760834-Pentyl-2-cyanopyridineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Methoxypyridine-2-carboxylic acid, compound 10(b) (R9=methoxy), was made employing Method P. To trimethylsilyl cyanide (0.95 g, 9.6 mmol), 4-methoxypyridine N-oxide (1 g, 8 mmol) in DCM (10 mL) was added, followed by dimethylcarbamoyl chloride (1.03 g, 9.6 mmol) in DCM (10 mL), dropwise. After stirring at room temperature overnight, sodium bicarbonate (100 mL, 10%) was added, and the organic layer was separated. The aqueous layer was extracted twice by DCM (50 mL each). The combined organic layer was dried over magnesium sulfate and the solvent was removed to obtain product, compound 10a (0.97 g, 90%):

Aufarbeitung

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice by DCM (50 mL each)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-11db0f0b3eac45f280ac931cb2145e6a
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199105B2

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