Reaction #5533

Reaction equation

5-mercaptoimidazo[1,2-a]pyridine

1-bromo-3-chloropropane

triethylamine

→

desired product

Yield 72.1%

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

Yield 72.1%

Solvents

ethanol

Conditions

Workup

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONchloroform was added to the residue, which
3. 3
   Washwas washed with water
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONAfter the solvent was distilled off
6. 6
   Otherthe residue was purified by column chromatography (eluent: ethyl acetate)

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (5.02 g, 33.4 mmoles) and 1-bromo-3-chloropropane (5.26 g, 33.4 mmoles) in ethanol (100 ml) was added triethylamine (4.66 ml, 33.4 mmoles) and the mixture was stirred at room temperature for 17 hours. After the solvent was distilled off, chloroform was added to the residue, which was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 5.46 g of the desired product (72.0%, light brown oily product).

Source