Dichloromethane → 2-cyclopropylmethyl-4-methanesulfonyloxymethyl-6-[4-(methyl-sulfonyl)phenyl]-2H-pyridazin-3-one

HRID 1348751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1348751
[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]1

Komponenten

5

Edukt 4

HCID 6344Dichloromethane2×HCID 70297m-Chloroperbenzoic acidHCID 219915572-cyclopropylmethyl-4-methanesulfonyloxymethyl-6-[4-(methyl thio)phenyl]-2H-pyridazin-3-oneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 219916462-cyclopropylmethyl-4-methanesulfonyloxymethyl-6-[4-(methyl-sulfonyl)phenyl]-2H-pyridazin-3-oneAusbeute 85,3 %

Versuchsvorschrift

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%).

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was successively washed with a saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from chloroform-hexane

Quellen und Nachweise

ORD-Eintrag
ord-bb6b281b7518495b984c28e346d77ccb
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211577B2

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