Sodium Thiosulfate → HCID 66968532, compound

HRID 2095785Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][C:9]=2[CH3:16])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[CH3:16][C:9]1[C:8]([C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[N+:13]([O-:25])[C:12]([C:14]#[N:15])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 6-(4-fluorophenyl)-5-methylpyridine-2-carbonitrile (750 mg, 3.86 mmol) and m-chloroperbenzoic acid (purity 69%, 2.4 g, 96.5 mmol) in tetrahydrofuran (8 mL) was stirred with heating at 50° C. for 3 days. Saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3→1/2) to give the title compound (74.8 mg, 9%) as white crystals.

Workup

extractionthe mixture was extracted 3 times with ethyl acetate
washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3→1/2)

Sources & evidence

ORD record: ord-9539928ba1b64c479a9ca855972f96a7
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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