Sodium Thiosulfate → 4-(5-methyl-1,3,4-oxadiazol-2-yl)-N-[4-(methylsulfonyl)phenyl]pyridin-2-amine

HRID 452771Notes

Reaction equation

HRID 452771 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][C:17](SC)=[CH:16][CH:15]=3)[CH:8]=2)=[N:4][N:3]=1.Cl[C:23]1C=CC=C(C(OO)=O)C=1.[S:33]([O-:37])([O-])(=[O:35])=S.[Na+].[Na+]>CN(C)C(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([S:33]([CH3:23])(=[O:37])=[O:35])=[CH:18][CH:19]=3)[CH:8]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 686633194-(5-methyl-1,3,4-oxadiazol-2-yl)-N-[4-(methylthio)phenyl]pyridin-2-amine

Product 1

HCID 686635574-(5-methyl-1,3,4-oxadiazol-2-yl)-N-[4-(methylsulfonyl)phenyl]pyridin-2-amineYield 43%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(5-methyl-1,3,4-oxadiazol-2-yl)-N-[4-(methylthio)phenyl]pyridin-2-amine (441 mg, 1.48 mmol) in N,N-dimethylacetamide (5 mL) was added m-chloroperbenzoic acid (70%, 531 mg, 2.22 mmol) at room temperature, and the resulting mixture was stirred for 1 hr. A saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was stirred for 15 min and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) and recrystallized from hexane/tetrahydrofuran to give the title compound (213 mg, yield 43%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-14733de5b33f441881869a39470e8a0b
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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