Sodium hydride → 2-Cyano-6-[2-(N,N-dimethylamino)ethyl]thiopyridine

HRID 499380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499380
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][SH:5].[H-].[Na+].Cl[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[N:11]=1>O1CCCC1>[C:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([S:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[N:11]=1)#[N:17]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 25799CaptamineHCID 1184246-Chloropyridine-2-carbonitrile

Produkt 1

HCID 684549672-Cyano-6-[2-(N,N-dimethylamino)ethyl]thiopyridineAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Dimethylaminoethanethiol (0.71 g, 5.0 mmol) was dissolved in tetrahydrofuran (100 ml) and added dropwise to sodium hydride (60% oil, 0.44 g, 11.0 mmol). The reaction mixture was stirred at room temperature for 1 hr. A solution of 2-chloro-6-cyanopyridine (0.70 g, 5.0 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure to give the titled compound (0.49 g, 47%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 18 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. customdried
  7. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bf6a4391f9e145099f13c4d31a6bce2c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767665B2

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