Réaction #5564

Équation de réaction

5-[3-[2-(phenylamino)ethyloxy]propylthio]imidazo[1,2-a]pyridine

triethylamine

methanesulfonyl chloride

→

desired product

Rendement 1.2%

5-[3-[2-(N-methanesulfonylanilino)ethyloxy]propylthio]imidazo[1,2-a]pyridine

Rendement 1.2%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture was further stirred under ice-
3. 3
   Températurecooling for 10 minutes
4. 4
   LavageThe reaction mixture was washed with water
5. 5
   Extractionthe aqueous layer was extracted with methylene chloride (30 ml×3)
6. 6
   Séchagedried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONAfter the solvent was distilled off
8. 8
   Autrethe residue was purified by column chromatography (eluent: ethyl acetate)

Mode opératoire

To a solution of 5-[3-[2-(phenylamino)ethyloxy]propylthio]imidazo[1,2-a]pyridine (1.034 g, 3.158 mmoles) and triethylamine (0.88 ml, 6.3 mmoles) in methylene chloride (30 ml) was added methanesulfonyl chloride (0.37 ml, 4.7 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 10 minutes. The reaction mixture was washed with water and the aqueous layer was extracted with methylene chloride (30 ml×3). The methylene chloride layers were combined and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 16 mg of the desired product (brown oily product)

Source