1-Pentanethiol → 2-Cyano-6-pentylthiopyridine

HRID 748193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748193
[CH2:1]([SH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[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:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[N:11]=1)#[N:17]

Komponenten

5

Edukt 3

HCID 80671-PentanethiolHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrile

Produkt 1

HCID 229392832-Cyano-6-pentylthiopyridineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Pentyl 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-960a4b4dba324bd5ae9ad4148c8f6267
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399759B2

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