Phosphorus oxychloride → HCID 57486566, compound
Reaction equation
P(Cl)(Cl)(Cl)=[O:2].ClC1[N+]([O-])=N[C:10]([O:14][C:15]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:16]=2[CH2:17][C:18]3([CH3:24])C)=CC=1.[Cl:25][C:26]1N=[N+]([O-])C(OC2C=CC=C3C=2CC3(C)C)=C[CH:31]=1>>[Cl:25][CH2:26][CH2:31][CH2:24][CH:18]1[C:19]2[C:16](=[C:15]([O:14][CH3:10])[CH:22]=[CH:21][CH:20]=2)[C:17]1=[O:2]Participants
Procedure
0.50 mL (5.4 mmol) of phosphorus oxychloride was added to 61.7 mg (0.223 mmol) of a mixture of 6-chloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]-pyridazine 1-oxide and 3-chloro-6-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine 1-oxide obtained in (4), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layers were combined, washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by preparative thin-layer chromatography (developed by hexane:ethyl acetate=5:1) to obtain 43.7 mg (0.148 mmol, Yield: 66.4%) of 4,6-dichloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine.
Sources & evidence
- ORD record
- ord-5f348c0152e64ec39da9c2b6af9fb6af
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608563B2
Reaction notes
Loading…