Reaktion #53366

Reaktionsgleichung

diethyl azodicarboxylate

compound

1-{6-[(6-Chloropyridazin-3-yl)-hydrazono-(4-nitrophenyl)-methyl]-(benzo-1,3-dioxol-5-yl)}-propan-2-ol

triphenyiphosphine

→

title compound

Ausbeute 42.0%

(±)-7-(3-Chloropyridazin-6-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Ausbeute 42.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 24 h
3. 3
   FiltrationAfter dilution with sodium chloride solution the precipitated product was filtered off
4. 4
   Sonstigedried
5. 5
   Sonstigepurified by column chromatography
6. 6
   workup.ADDITIONa mixture of chloroform-methanol (99:1) as eluent
7. 7
   SonstigeThe residue obtained on concentration
8. 8
   Sonstigewas crystallized
9. 9
   Temperaturby refluxing in ethanol

Vorschrift

A mixture of 0.3 g (0.66 mmol) of the compound prepared in Step A, 10 ml of dimethylformamide and 0.34 g (1.30 mmol) of triphenyiphosphine was stirred at room temperature for 5 min, then 0.20 ml (1.27 mmol) of diethyl azodicarboxylate was added and stirring was continued for 24 h. After dilution with sodium chloride solution the precipitated product was filtered off, dried and purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of chloroform-methanol (99:1) as eluent. The residue obtained on concentration was crystallized by refluxing in ethanol to yield 0.12 g (42%) of the title compound; Mp.: 254-255° C.

Quelle