Sodium Sulfite → 6-Chloro-3-[2-(methylsulfonyl)phenoxy]pyridazine 1-oxide

HRID 2424279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2424279
[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]=1

Komponenten

5

Edukt 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 229399336-Chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine 1-oxide

Produkt 1

HCID 229400506-Chloro-3-[2-(methylsulfonyl)phenoxy]pyridazine 1-oxideAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added to the solution
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe obtained residue was purified by preparative thin-layer chromatography (available from Merck Co., 1.05744, developed by hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-571933fd2fb24fb3abb41d1643d1f9b1
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964531B2

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