Benzoyl chloride → 1,2,4-Triazolo(4,3-b)pyridazine, 6-(4-morpholinyl)-3-phenyl-
Reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1)[NH2:2].[C:15](Cl)(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>>[O:12]1[CH2:11][CH2:10][N:9]([C:6]2[CH:7]=[CH:8][C:3]3[N:4]([C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:2][N:1]=3)[N:5]=2)[CH2:14][CH2:13]1Participants
Procedure
39 Grams of 3-hydrazino-6-morpholinopyridazine is added portionwise to 30 grams of benzoyl chloride. The mixture is heated at a temperature of 130°-140° C. for 1 hour. The mixture is then cooled and the residue of the reaction mixture is neutralized by the addition of aqueous sodium bicarbonate solution. The resulting aqueous mixture is then extracted with chloroform. The chloroform extract is washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The 6-morpholino-3-phenyl-s-triazolo[4,3-b]pyridazine product is obtained as a residue from the evaporation. The product is crystallized twice from isopropanol and found to melt at 195°-196° C. 15 Grams of the named product are obtained. The structure of the product is confirmed by infrared spectroscopy and by nuclear magnetic resonance analysis.
Workup
- temperatureThe mixture is heated at a temperature of 130°-140° C. for 1 hour
- temperatureThe mixture is then cooled
- extractionThe resulting aqueous mixture is then extracted with chloroform
- extractionThe chloroform extract
- washis washed with water
- dry with materialdried over anhydrous sodium sulfate
- customevaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-df6caeb9df6144468ebdc9a80feea19f
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04016162
Reaction notes
Loading…