Dichloromethane → 2-cyclopropylmethyl-4-methanesulfonyloxymethyl-6-[4-(methyl-sulfonyl)phenyl]-2H-pyridazin-3-one
Reaction equation
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][O:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8]C(C3C=CC(SC)=CC=3)=[N:6]2)[CH2:3][CH2:2]1.Cl[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33](OO)=O)[CH:28]=1.[S:37]([O-:40])(O)=[O:38].[Na+].[CH2:42](Cl)Cl>>[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][O:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:8][C:33]([C:29]3[CH:28]=[CH:27][C:32]([S:37]([CH3:42])(=[O:40])=[O:38])=[CH:31][CH:30]=3)=[N:6]2)[CH2:2][CH2:3]1Participants
Reactant 4
Product 1
Procedure
To a solution of 2-cyclopropylmethyl-4-methanesulfonyloxymethyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one (226 mg, 0.59 mmol) in methylene chloride (10 mL) was added dropwise at −20° C. a solution of 3-chloroperbenzoic acid (410 mg, 2.38 mmol) in methylene chloride (2 mL), and at the same temperature, the mixture was stirred for 30 minutes. A 10% aqueous sodium hydrogensulfite was added to the reaction mixture, and then, the mixture was extracted with chloroform. The extract was successively washed with a saturated aqueous sodium hydrogencarbonate and brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from chloroform-hexane to yield the title compound as a colorless crystalline powder (209 mg, 85.3%).
Workup
- extractionthe mixture was extracted with chloroform
- washThe extract was successively washed with a saturated aqueous sodium hydrogencarbonate and brine
- dry with materialwas then dried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customThe residue was recrystallized from chloroform-hexane
Sources & evidence
- ORD record
- ord-bb6b281b7518495b984c28e346d77ccb
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211577B2
Reaction notes
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