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

HRID 53213

Reaction equation

HRID 53213 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:23]=[C:22]([CH3:24])[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:10]([CH3:25])[CH:9]=2)[N:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>C(Cl)Cl>[F:27][C:2]([F:1])([F:26])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:23]=[C:22]([CH3:24])[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[N+:18]([O-:33])[CH:19]=[CH:20][CH:21]=3)=[C:10]([CH3:25])[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 190820123-[3-[4-(5-Trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine

Product 1

HCID 190820473-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine-N-oxideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine (1 g, 2.6 mmol) in 50 ml of methylene chloride cooled to 0° C. was added 0.67 g (3.9 mmol) of m-chloroperoxybenzoic acid, and the mixture was allowed to stir overnight. The mixture was washed with saturated sodium bicarbonate, the organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 1 g (98%) of 3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine-N-oxide, as a yellow oil which crystallized (yellow flakes) on standing, m.p. 84°-86°C.

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe1db43cea1c474a8266e236ad17c1b4
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Linked notes

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