Reaction #4486

Reaction equation

N-Bromosuccinimide

5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione

α,α'-azobisisobutyronitrile

→

5-{4-[2-(5-bromomethyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperatureunder reflux
2. 2
   TemperatureAfter refluxing for another 10 minutes
3. 3
   Washthe reaction mixture was washed with water
4. 4
   Dryingdried (MgSO4)
5. 5
   workup.DISTILLATIONThe solvent was distilled off

Procedure

N-Bromosuccinimide (2.75 g) was added portionwise to a solution of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (6.0 g) and α,α'-azobisisobutyronitrile (0.5 g) in carbon tetrachloride(150 ml) under reflux. After refluxing for another 10 minutes, the reaction mixture was washed with water and dried (MgSO4). The solvent was distilled off to give 5-{4-[2-(5-bromomethyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione as a crude oily substance (about 8 g). IR (neat) cm-1 : 1750, 1690. NMRδ(ppm) in CDCl3 : 3.03 (2 HtJ=7 Hz), 2.9 to 3.2 (1H, m), 3.48 (1H, d.d, J=14 and 5 Hz), 4.24 (2H, t, J=7 Hz), 4.45 (1h, d.d, J=9 and 5 Hz), 4.61 (2H, s), 6.81 (2H, d, J=9 Hz), 7.10 (2H, d, J=9 Hz), 7.4 (3H, m), 8.0 (2H, m), 8.70 (1H, broad s).

Source