Dimethylcarbamoyl Chloride → 5-Methoxy-6-methylpicolinonitrile

HRID 398253

Reaktionsgleichung

Reaktionsgleichung von HRID 398253
[CH3:1][O:2][C:3]1[C:4]([CH3:10])=[N+:5]([O-])[CH:6]=[CH:7][CH:8]=1.[C:11]([Si](C)(C)C)#[N:12].CN(C)C(Cl)=O>ClCCl>[C:11]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:10])[N:5]=1)#[N:12]

Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 122140163-Methoxy-2-methylpyridine 1-oxide

Produkt 1

HCID 230024175-Methoxy-6-methylpicolinonitrileAusbeute 11,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution obtained by dissolving 3-methoxy-2-methyl-pyridine-N-oxide (1.57 g, 11.3 mmol) in 30 ml of dichloromethane were added cyanotrimethylsilane (1.12 g, 11.3 mmol) and dimethylcarbamoyl chloride (1.21 g, 11.3 mmol), followed by stirring at room temperature for 9 days. The reaction solution was washed with 10% sodium carbonate aqueous solution and then with water. The organic layer was dried with sodium sulfate and concentrated to remove the solvent, by which 0.198 g (percent yield: 11.8%) of 2-cyano-5-methoxy-6-methylpyridine was obtained.

Aufarbeitung

  1. customTo a solution obtained
  2. washThe reaction solution was washed with 10% sodium carbonate aqueous solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated
  5. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-1d1b1b0466054e788516132c7d0acd6c
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610853B1

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