Reaktion #4485

Reaktionsgleichung

2-imino-5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-thiazolidinone

H2SO4

dioxane

→

5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione

Ausbeute 58.8%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous mixture was extracted with chloroform
2. 2
   WaschenThe chloroform layer was washed with water
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe oily residue was chromatographed on a column of silica gel (200 g)
6. 6
   Waschenfrom the fractions eluted with chlorform-methanol (100:1, V/V)

Vorschrift

A mixture of 2-imino-5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-thiazolidinone (11.4 g), 1N.H2SO4 (100 ml) and dioxane (100 ml) was stirred at 80° C. for 5 hours, and poured in water. The aqueous mixture was extracted with chloroform. The chloroform layer was washed with water, dried (MgSO4) and concentrated. The oily residue was chromatographed on a column of silica gel (200 g), and from the fractions eluted with chlorform-methanol (100:1, V/V), there was obtained 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione (6.7 g, 58.8%). Recrystallization from ethyl acetate-hexane afforded colorless plates. m.p. 162°-163° C. Elemental analysis for C21H18N2O4S, Calcd.: C, 63.95; H, 4.60; N, 7.10. Found: C, 63.84; H, 4.63; N, 6.90. This product showed the IR and NMR spectra in accordance with those of the compound obtained in Example 6.

Quelle