反応 #63907

反応方程式

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

thiosemicarbazide

→

desired compound

収率 25.3%

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

収率 25.3%

溶媒

ethanol

反応条件

後処理

1. 1
   その他the solvent was removed in vacuo
2. 2
   workup.ADDITIONTo the residue was added 100 ml of glacial acetic acid
3. 3
   温度this mixture was refluxed 18 hours
4. 4
   その他the acetic acid was removed in vacuo
5. 5
   workup.ADDITIONSaturated aqueous sodium bicarbonate was added
6. 6
   抽出was then extracted with dichloromethane:methanol (9:1)
7. 7
   洗浄The extract was washed with water
8. 8
   その他dried
9. 9
   その他evaporated
10. 10
    その他The residue was chromatographed on a silica gel column
11. 11
    洗浄eluting with dichloromethane:methanol (9:1)
12. 12
    その他The product was crystallized from dichloromethane-hexane

実験手順

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.

出典