Reaktion #63821

Reaktionsgleichung

4-chloronicotinic acid

4-methoxybenzylmercaptan

sodium hydride

→

4-(4-methoxybenzylthio)-nicotinic acid

Lösungsmittel

—

ice water

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturice-cooled
2. 2
   Sonstigeprepared by the process
3. 3
   workup.STIRRINGThe reaction was stirred at room temperature for 4 hours during which a thick solid
4. 4
   Sonstigeformed
5. 5
   ExtraktionAfter extraction with 25 mL of hexane
6. 6
   Sonstigeto precipitate 4-(4-methoxybenzylthio)-nicotinic acid

Vorschrift

A stirred and ice-cooled mixture of 788 mg (0.005 mole) 4-chloronicotinic acid [prepared by the process set forth in W. C. J. Ross, J. Chem. Soc.(C), 1816 (1966)]and 771 mg (0.005 mole) of 4-methoxybenzylmercaptan in 6 mL of dry N,N-dimethylformamide was treated with 480 mg (0.012 mole) of 60% sodium hydride dispersion. The reaction was stirred at room temperature for 4 hours during which a thick solid formed, which was taken up in 75 mL of ice water. After extraction with 25 mL of hexane, the aqueous layer was acidified with 2.5N hydrochloric acid to precipitate 4-(4-methoxybenzylthio)-nicotinic acid; yield 1.2 g (89% of theory), m.p. 230° C.

Quelle