Phosphorus oxychloride → 3-Chloro-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:10][C:11]2[N:12]([C:14](=O)[NH:15][N:16]=2)[N:13]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:14]1[N:12]2[N:13]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[CH:10][C:11]2=[N:16][N:15]=1Participants
3
Conditions
- Temperature
- 130 °C
Procedure
A suspension of 6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (1.0 g, 2.8 mmol) in phosphorus oxychloride (10 mL) was stirred at 130° C. for 6 h. Analysis by HPLC/MS indicated the starting material had been consumed. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with CH2Cl2, the resulting solution washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (Na2SO4) and concentrated under reduced pressure to afford 1.1 g (100%) of the title compound as an off-white solid. HPLC/MS (method A): retention time=3.52 min, (M+H)+=375.0.
Workup
- customhad been consumed
- temperatureAfter cooling to room temperature
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionThe obtained residue was diluted with CH2Cl2
- washthe resulting solution washed with saturated aqueous NaHCO3, saturated aqueous NaCl
- dry with materialdried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ebbc5bb71d684175a005ec7725b8faf3
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632837B2
Reaction notes
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