Reacción #53366

Ecuación de reacción

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

Rendimiento 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

Rendimiento 42.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente