m-Chloroperbenzoic acid → 6-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine-N-oxide

HRID 963328Notes

Reaction equation

HRID 963328 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([C:19]3[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[O:21][N:20]=3)=[CH:14][C:13]=2[CH3:28])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N+:7]([O-:37])=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:13]([CH3:28])=[CH:14][C:15]([C:19]3[N:23]=[C:22]([C:24]([F:26])([F:25])[F:27])[O:21][N:20]=3)=[CH:16][C:17]=2[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10091835HCID 10091835, compound

Product 1

HCID 190820506-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine-N-oxideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.08 g (2.8 mmol) of 6-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine in 30 ml of methylene chloride was added 0.71 g (1.5 eq) or m-chloroperbenzoic acid (MCPBA). The mixture was stirred under nitrogen for 18 h at room temperature, poured into saturated sodium bicarbonate solution, and the organic layer was separated and dried over sodium sulfate. The organic layer was filtered, concentrated, and the residue was recrystallized from isopropyl acetate/hexane to afford 0.93 g (83%) of 6-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine-N-oxide, as white needles, m.p. 119°-121° C.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationThe organic layer was filtered
  4. concentrationconcentrated
  5. customthe residue was recrystallized from isopropyl acetate/hexane

Sources & evidence

ORD record
ord-c703eaf79670473ba318edbba2df2429
Source dataset
uspto-grants-1998_06
Patent number
US05763461

Reaction notes

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