m-Chloroperbenzoic acid → HCID 22272627, compound

HRID 1064866Notes

Reaction equation

HRID 1064866 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[C:7]([S:15][CH3:16])=[N:8][C:9]([CH3:14])=[CH:10][C:11]=1[S:12][CH3:13])=[O:4].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)(Cl)Cl.O>[Br:1][CH2:2][C:3]([NH:5][C:6]1[C:7]([S:15]([CH3:16])=[O:25])=[N:8][C:9]([CH3:14])=[CH:10][C:11]=1[S:12][CH3:13])=[O:4]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 222471492-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamide

Product 1

HCID 22272627HCID 22272627, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide (100 mg,0.311 mmol) in chloroform (2 ml) was added a solution of m-chloroperbenzoic acid (50 mg, 0.327 mmol) in chloroform (0.5 ml), and stirred at room temperature for 17 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution, water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:acetone=1:1) to provide 21.4 mg (yield 20%) of 2-bromo-N-[2(methanesulfinyl)-6-methyl-4-(methylthio)-3-pyridyl]acetamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium bicarbonate solution, water
  3. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:acetone=1:1)

Sources & evidence

ORD record
ord-0699c7a32b85438ba78892e52a2bb306
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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