m-Chloroperbenzoic acid → N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

HRID 1922198Notes

Reaction equation

HRID 1922198 reaction equation
[CH3:1][S:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)=[O:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 577256324-(2-(methylthio)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

Product 1

HCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the 4-(2-(methylthio)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide (1.26 g, 4.0 mmol, 1.0 eq) in 40 mL of methylene chloride was added 3-chloroperoxybenzoic acid (70%, 989 mg, 4.4 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for 5 hours and then was diluted with 200 mL of methylene chloride. The resulting mixture was washed with aqueous sodium bicarbonate and brine then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was used to next step without further purification. MH+=332.

Workup

  1. washThe resulting mixture was washed with aqueous sodium bicarbonate and brine
  2. dry with materialthen dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give crude product, which
  6. customwas used to next step without further purification

Sources & evidence

ORD record
ord-1196ce5d76a446caa5260bbbb85b5823
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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