反应 #4486

反应方程式

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

溶剂

carbon tetrachloride

反应条件

后处理

1. 1
   温度under reflux
2. 2
   温度After refluxing for another 10 minutes
3. 3
   洗涤the reaction mixture was washed with water
4. 4
   干燥dried (MgSO4)
5. 5
   workup.DISTILLATIONThe solvent was distilled off

实验过程

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).

来源