反応 #63909

反応方程式

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

thiosemicarbazide

→

desired compound

収率 14.0%

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

収率 14.0%

溶媒

ethanol

反応条件

後処理

1. 1
   その他evaporated in vacuo
2. 2
   workup.ADDITIONTo the residue was added 100 ml of glacial acetic acid
3. 3
   温度This mixture was refluxed overnight
4. 4
   その他the solvent was removed in vacuo, 150 ml of water
5. 5
   workup.ADDITIONadded
6. 6
   workup.ADDITIONaqueous sodium bicarbonate added
7. 7
   抽出This mixture was extracted with dichloromethane:methanol (9:1)
8. 8
   その他The extracts were 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
    workup.ADDITIONThe fractions containing product
13. 13
    その他evaporated
14. 14
    その他The residue was chromatographed on silica gel thick layer preparative plates with dichloromethane:methanol (95:5)
15. 15
    その他to give yellow crystals
16. 16
    その他Recrystallization from dichloromethane-ether-hexane

実験手順

A solution of 2.0 g of N-ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide and 1.32 g of thiosemicarbazide in 100 ml of ethanol was refluxed for 8 hours, then evaporated in vacuo. To the residue was added 100 ml of glacial acetic acid. This mixture was refluxed overnight, then the solvent was removed in vacuo, 150 ml of water added and aqueous sodium bicarbonate added to neutralize the solution. This mixture was extracted with dichloromethane:methanol (9:1). The extracts were dried and evaporated. The residue was chromatographed on a silica gel column eluting with dichloromethane:methanol (9:1). The fractions containing product were combined and evaporated. The residue was chromatographed on silica gel thick layer preparative plates with dichloromethane:methanol (95:5) to give yellow crystals. Recrystallization from dichloromethane-ether-hexane gave 0.3 g of the desired compound as yellow crystals, mp 192°-193° C.

出典