Isoamyl mercaptan → 2-Cyano-6-isopentylthiopyridine

HRID 748195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748195
[CH2:1]([SH:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[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:6][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[N:11]=1)#[N:17]

Komponenten

5

Edukt 3

HCID 10925Isoamyl mercaptanHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrile

Produkt 1

HCID 229393372-Cyano-6-isopentylthiopyridineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Isopentyl mercaptan (0.83 g, 7.9 mmol) was dissolved in tetrahydrofuran (100 ml) and added dropwise to sodium hydride (60% oil, 0.35 g, 8.7 mmol). The reaction mixture was stirred at room temperature for 1 hr. A solution of 2-chloro-6-cyanopyridine (1.00 g, 7.2 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 (1.48 g, ca. 100%) as an oil.

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-019720b020094960af8d57165c8926ac
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399759B2

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