Reacción #80416

Ecuación de reacción

2-hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

Thionyl chloride

→

2-chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   OtroAfter the completion of the reaction
3. 3
   workup.DISTILLATIONthe thionyl chloride was distilled away
4. 4
   Extracciónextracted with chloroform
5. 5
   SecadoThe chloroform layer was dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled away

Procedimiento

Thionyl chloride (20 ml) was dropwise added to 2-hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine (2 g) under ice-cooling and the mixture was stirred at room temperature for 1.5 hours. After the completion of the reaction, the thionyl chloride was distilled away. The residue was alkali-oversaturated with potassium carbonate and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to give 2.1 g of 2-chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine as an oily substance. The oily substance was added to ethanol (50 ml) containing a solution of 2-mercaptobenzimidazole (1.0 g) and sodium hydroxide (0.6 g) in water (10 ml) and the mixture was refluxed under heating for 5 hours. After the completion of the reaction, the ethanol was distilled away and water was added to the residue, followed by extraction with chloroform. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled away. Acetone was added to the residue to allow crystallization. The obtained crystals were recrystallized from a mixed solvent of ethanol-acetone to give 2-((3-methyl-4-(2-morpholinoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole as white crystals, melting point 201°-203° C.

Fuente