Réaction #1168915

Équation de réaction

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

triethylamine

benzoyl chloride

→

desired product

Rendement 88.1%

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

Rendement 88.1%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was further stirred at room temperature for 30 minutes
2. 2
   LavageThe reaction mixture was washed with an aqueous 1N sodium hydroxide solution
3. 3
   Autredried
4. 4
   workup.DISTILLATIONAfter the solvent was distilled off
5. 5
   Autrethe residue was purified by column chromatography [eluent:hexane/acetone (1:1)]

Mode opératoire

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added benzoyl chloride (1.10 ml, 11.6 moles) with stirring at room temperature and the mixture was further stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous 1N sodium hydroxide solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent:hexane/acetone (1:1)] to obtain 1.32 g of the desired product (88.1%, white solid).

Source