Réaction #317974

Équation de réaction

4-mercaptobenzenecarboxylic acid

2-chloromethylpyridine hydrochloride

potassium carbonate

→

compound

Rendement 40.9%

4-(pyridin-2-ylmethylsulfanyl)benzenecarboxylic acid

Rendement 40.9%

Solvants

ethanol water

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 4 hours
2. 2
   AutreThe organic solvent was evaporated off under reduced pressure, and aqueous 5 N hydrochloric acid solution
3. 3
   workup.ADDITIONwas added to the residue until it
4. 4
   AutreWater was evaporated off under reduced pressure, and DMF
5. 5
   workup.ADDITIONwas added to the resulting residue
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure
8. 8
   Autrethe resulting residue was purified through silica gel column chromatography (chloroform/methanol=9/1 to 4/1)

Mode opératoire

An ethanol/water mixed solution (2/1, 60 mL) of 4-mercaptobenzenecarboxylic acid (1.0 g), 2-chloromethylpyridine hydrochloride (2.1 g) and potassium carbonate (4.5 g) was heated under reflux for 4 hours. The organic solvent was evaporated off under reduced pressure, and aqueous 5 N hydrochloric acid solution was added to the residue until it became acidic. Water was evaporated off under reduced pressure, and DMF was added to the resulting residue and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform/methanol=9/1 to 4/1) to obtain the entitled compound (650 mg).

Source