Reaktion #53357

Reaktionsgleichung

(R)—N′-(8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-7-carbothioyl)-acetic hydrazide

ethanol

→

title compound

Ausbeute 51.0%

(R)-8-Methyl-5-(4-nitrophenyl)-7-(5-methyl-1,3,4-oxadiazol-2-yl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Ausbeute 51.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 2 h
2. 2
   SonstigeThe residue obtained on concentration
3. 3
   Filtrationfiltered through a neutral aluminum oxide column
4. 4
   WaschenAfter washing the column the filtrate
5. 5
   Einengenwas concentrated
6. 6
   Sonstigethe residue was purified by column chromatography
7. 7
   workup.ADDITIONa mixture of n-hexane-ethyl acetate (1:2.5) as eluent

Vorschrift

A stirred mixture of 2.2 g (5.15 mmol) of (R)—N′-(8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-7-carbothioyl)-acetic hydrazide (an intermediate of method B of Example 28), 44 ml of ethanol and 1.72 g (5.39 mmol) of mercury (II) acetate was refluxed for 2 h. The residue obtained on concentration was dissolved in dichloromethane and filtered through a neutral aluminum oxide column. After washing the column the filtrate was concentrated and the residue was purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of n-hexane-ethyl acetate (1:2.5) as eluent to yield 1.07 g (51%) of the title compound. Mp.: 202-204° C. after recrystallization from ethanol. [α]: −249° (c=0.22; CHCl3).

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