Reaktion #6262

Reaktionsgleichung

4-mercaptopyridine

N-(hydroxymethyl)nicotinamide

→

desired compound

Ausbeute 15.9%

4-(3-picolinoylaminomethylthio)pyridine

Ausbeute 15.9%

Lösungsmittel

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.DISTILLATIONThe solvent was distilled off
3. 3
   workup.ADDITION30 ml of ethanol was added to the residue
4. 4
   workup.DISTILLATIONThe solvent was distilled off
5. 5
   workup.ADDITIONwater was added to the residue
6. 6
   Extraktionfollowed by extraction with chloroform
7. 7
   WaschenAfter washing with saturated saline
8. 8
   Trocknenthe extract was dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off
10. 10
    Sonstigethe residue was purified by column chromatography (eluent: ethyl acetate/ethanol =5:1)

Vorschrift

To a mixture of 1.11 g (10 mmol) of 4-mercaptopyridine and 1.52 g (10 mmol) of N-(hydroxymethyl)nicotinamide, 30 ml of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off and 30 ml of ethanol was added to the residue. The solvent was distilled off and water was added to the residue. The mixture was neutralized with saturated aqueous sodium bicarbonate, followed by extraction with chloroform. After washing with saturated saline, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol =5:1) to give 390 mg of the desired compound (15.9% yield, yellow solid).

Quelle