Reacción #63907

Ecuación de reacción

N-methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

thiosemicarbazide

→

desired compound

Rendimiento 25.3%

N-Methyl-N-[3-(3-amino-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide

Rendimiento 25.3%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed in vacuo
2. 2
   workup.ADDITIONTo the residue was added 100 ml of glacial acetic acid
3. 3
   Temperaturathis mixture was refluxed 18 hours
4. 4
   Otrothe acetic acid was removed in vacuo
5. 5
   workup.ADDITIONSaturated aqueous sodium bicarbonate was added
6. 6
   Extracciónwas then extracted with dichloromethane:methanol (9:1)
7. 7
   LavadoThe extract was washed with water
8. 8
   Otrodried
9. 9
   Otroevaporated
10. 10
    OtroThe residue was chromatographed on a silica gel column
11. 11
    Lavadoeluting with dichloromethane:methanol (9:1)
12. 12
    OtroThe product was crystallized from dichloromethane-hexane

Procedimiento

A solution of 2.2 g of N-methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide and 1.5 g of thiosemicarbazide in 100 ml of ethanol was refluxed for 5 hours, then the solvent was removed in vacuo. To the residue was added 100 ml of glacial acetic acid, this mixture was refluxed 18 hours, then the acetic acid was removed in vacuo. Saturated aqueous sodium bicarbonate was added to neutralize the mixture which was then extracted with dichloromethane:methanol (9:1). The extract was washed with water, dried and evaporated. The residue was chromatographed on a silica gel column, eluting with dichloromethane:methanol (9:1). The product was crystallized from dichloromethane-hexane, giving 0.6 g of the desired compound as yellow crystals mp 196°-197° C.

Fuente