Reaktion #1663685

Reaktionsgleichung

3-cyano-1-methyl-1,2,5,6-tetrahydropyridine

thiophenol

pyridine

→

title compound

1-Methyl-4-phenylmercaptonipecotonitrile

Lösungsmittel

dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 110°
2. 2
   workup.STIRRINGwith stirring for 24 hours
3. 3
   SonstigeThe solvent was removed in vacuo
4. 4
   workup.ADDITIONthe residual brown oil diluted with benzene (100 ml.)
5. 5
   Waschenwashed with N/1 hydrochloric acid (3 × 25 ml.)
6. 6
   Extraktionextracted into benzene (3 × 25 ml)
7. 7
   WaschenThe combined extracts were washed with saturated brine
8. 8
   Trocknendried (MgSO4)
9. 9
   Sonstigeevaporated
10. 10
    Sonstigeto give a residual solid
11. 11
    SonstigeRecrystallisation from benzene - 60°/80° petroleum ether

Vorschrift

A mixture of 3-cyano-1-methyl-1,2,5,6-tetrahydropyridine (6.1 g 0.05 m.) thiophenol (5.50 g., 0.05 m.) and pyridine (1 ml.) was stirred at room temperature for 1 hour, diluted with dioxan (7 ml.) and heated at 110° with stirring for 24 hours. The solvent was removed in vacuo and the residual brown oil diluted with benzene (100 ml.) washed with N/1 hydrochloric acid (3 × 25 ml.) and the combined washings made basic, with 2N sodium hydroxide and extracted into benzene (3 × 25 ml). The combined extracts were washed with saturated brine, dried (MgSO4) and evaporated to give a residual solid. Recrystallisation from benzene - 60°/80° petroleum ether gave the title compound as colourless plates (8 g., 75%) m.p. 114°C. Found: C, 67.42; H, 6.97; N, 11.99. C13H16N2S requires: C, 67.21; H, 6.94; N, 12.06%.

Quelle