Reaktion #55320

Reaktionsgleichung

potassium carbonate

propargyl chloride

4-mercaptopyridine

→

4-(2-propynylthio)pyridine

Ausbeute 40.2%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then cooled to room temperature
2. 2
   Filtrationfiltered
3. 3
   workup.ADDITIONThe filtrate was added to an equal volume of water
4. 4
   ExtraktionThis mixture was extracted with ether
5. 5
   SonstigeAfter removal of the ether under reduced pressure, there
6. 6
   workup.DISTILLATIONDistillation

Vorschrift

In 200 ml dimethyl sulfoxide (DMSO) was dissolved 25.0 g (0.225 mole) 4-mercaptopyridine. To this solution were added 15.5 g (0.112 mole) anhydrous potassium carbonate and 16.5 g (0.25 mole) propargyl chloride. This mixture was heated at 60° C. for 3 hours. The reaction mixture was then cooled to room temperature and filtered. The filtrate was added to an equal volume of water. This mixture was extracted with ether. After removal of the ether under reduced pressure, there remained 20.0 g crude product. Distillation gave 13.5 g 4-(2-propynylthio)pyridine. Yield 39% theory; b.p. 79°-81° C. (1.0 mm); mp 55°-56° C.

Quelle