Water → 8-[1-(4-Chlorophenoxy)ethyl]-1,2,4-triazolo[4,3-b]pyridazine
Reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH:7]([CH3:15])[C:8](=O)[CH:9]=[CH:10][N:11](C)C)=[CH:4][CH:3]=1.N[N:19]1[CH:23]=[N:22][N:21]=[CH:20]1.O>C(O)(=O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH:7]([C:8]2[C:23]3[N:19]([CH:20]=[N:21][N:22]=3)[N:11]=[CH:10][CH:9]=2)[CH3:15])=[CH:4][CH:3]=1Participants
Procedure
A solution of 4-(4-chlorophenoxy)-1-(dimethylamino)-1-penten-3-one (14.5 g) in glacial acetic acid (100 ml) was added dropwise to a solution of 4-amino-1,2,4-triazole (5.0 g) in glacial acetic acid (100 ml). The solution was boiled under reflux for 4 hours and then poured into water (400 ml). The mixture was extracted with toluene. The combined organic extracts were washed with 10% sodium bicarbonate solution, then with water, dried over anhydrous magnesium sulphate, filtered, and evaporated under reduced pressure. Flash column chromatography of the residue on silica gel, using ethyl acetate/petroleum ether 1:1 as the mobile phase, afforded 1.52 g of 8-[1-(4-chlorophenoxy)ethyl]-1,2,4-triazolo[4,3-b]pyridazine. A pure sample was obtained by recrystallisation from a mixture of ethyl acetate and hexane, m.p. 98-99° C.
Workup
- temperatureunder reflux for 4 hours
- extractionThe mixture was extracted with toluene
- washThe combined organic extracts were washed with 10% sodium bicarbonate solution
- dry with materialwith water, dried over anhydrous magnesium sulphate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-96f045e4efb44bd38afe36b1ec404787
- Source dataset
- uspto-grants-1999_05
- Patent number
- US05905079
Reaction notes
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