Réaction #4486

Équation de réaction

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

Solvants

carbon tetrachloride

Conditions de réaction

Traitement

1. 1
   Températureunder reflux
2. 2
   TempératureAfter refluxing for another 10 minutes
3. 3
   Lavagethe reaction mixture was washed with water
4. 4
   Séchagedried (MgSO4)
5. 5
   workup.DISTILLATIONThe solvent was distilled off

Mode opératoire

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