4-Chloro-2-pyridinecarbonitrile → 4-(Methylsulfanyl)pyridine-2-carbonitrile

HRID 1437240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437240
[CH3:1][S-:2].[Na+].Cl[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1>CN(C)C=O>[CH3:1][S:2][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1

Komponenten

4

Edukt 2

HCID 6933424-Chloro-2-pyridinecarbonitrileHCID 4378561Sodium methanethiolate

Produkt 1

HCID 203104474-(Methylsulfanyl)pyridine-2-carbonitrileAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium thiomethoxide (1.01 g) was added to 4-chloropyridine-2-carbonitrile (2.00 g) obtained from Referential Example 113 in N,N-dimethylformamide (20 mL) at 0° C., followed by stirring for 2 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid (1.96 g, 90%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. filtrationfollowed by filtration
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2eec23f02f314cc1b148f16b0d686b5e
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622471B2

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