Reaktion #4484

Reaktionsgleichung

2-imino-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-4-thiazolidinone

HCl

ethanol

→

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

Ausbeute 95.7%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 12 hours
3. 3
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
4. 4
   Extraktionextracted with chloroform
5. 5
   WaschenThe chloroform layer was washed with water
6. 6
   Trocknendried (MgSO4)
7. 7
   workup.DISTILLATIONThe solvent was distilled off

Vorschrift

A mixture of 2-imino-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-4-thiazolidinone (18.8 g), 2N-HCl (200 ml) and ethanol (200 ml) was heated under reflux for 12 hours. The solvent was distilled off under reduced pressure. The residue was neutralized with saturated aqueous solution of sodium hydrogen carbonate, and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4). The solvent was distilled off, whereby 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (18.0 g, 95.7%) was obtained. Recrystallization from ethanol afforded colorless needles. m.p. 113°-114° C. Elemental Analysis for C22H20N2O4S, Calcd.: C, 64.69; H, 4.93; N, 6.86. Found: C, 64.48; H, 4.91; N, 6.75.

Quelle