Water → 3-Chloro-6-(methylsulfonyl)pyridazine

HRID 909650

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5]([S:8][CH3:9])=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:18])C=1.[OH2:21]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([S:8]([CH3:9])(=[O:18])=[O:21])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Chloro-6-(methylthio)pyridazine (90 mg, 0.50 mmol) synthesized in Example (118b) was dissolved in methylene chloride (10 mL), and m-chloroperbenzoic acid (220 mg, 1.00 mmol) was added, followed by stirring at 0° C. for 30 minutes under nitrogen atmosphere. Water (20 mL) was added to the reaction solution, and extraction was carried out twice with methylene chloride (10 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-100%) to afford the desired compound (77 mg, yield 71%) as a white solid.

Workup

washThe organic layer was washed with saturated brine
dry with materialsubsequently dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified
washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-100%)

Sources & evidence

ORD record: ord-fbe7481ac3fd405184b10c8372aa077d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017610B2

Linked notes

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