Sodium Sulfite → 6-Chloro-3-[2-(methylsulfonyl)phenoxy]pyridazine 1-oxide
Reaction equation
[Cl:1][C:2]1[N+:7]([O-:8])=[N:6][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2SC)=[CH:4][CH:3]=1.Cl[C:19]1C=CC=C(C(OO)=O)C=1.[S:29]([O-:32])([O-])=[O:30].[Na+].[Na+]>ClCCCl>[Cl:1][C:2]1[N+:7]([O-:8])=[N:6][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:29]([CH3:19])(=[O:32])=[O:30])=[CH:4][CH:3]=1Participants
Procedure
In 1,2-dichloroethane (5 mL) was dissolved 208 mg (0.774 mmol) of 6-chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine 1-oxide obtained in Example 11 (1), 829 mg (3.84 mmol) of 80% m-chloroperbenzoic acid was added to the solution and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into 10% aqueous sodium sulfite solution, and extracted with ethyl acetate. The organic layers were combined, washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off and the obtained residue was purified by preparative thin-layer chromatography (available from Merck Co., 1.05744, developed by hexane:ethyl acetate=1:1) to obtain 132 mg (0.439 mmol, Yield: 56.7%) of 6-chloro-3-[2-(methylsulfonyl)phenoxy]pyridazine 1-oxide.
Workup
- additionwas added to the solution
- extractionextracted with ethyl acetate
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
- customthe obtained residue was purified by preparative thin-layer chromatography (available from Merck Co., 1.05744, developed by hexane:ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-c3c679b7915647d6aefb22a6a413adf1
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608563B2
Reaction notes
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