m-Chloroperbenzoic acid → 3-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine N-oxide

HRID 1957250Notes

Reaction equation

HRID 1957250 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[N+:4]([O-:29])[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 157668763-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine

Product 1

HCID 544650683-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine N-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.5 g (14 mmol) of 3-chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine and 9.7 g (31 mmol) of 3-chloroperbenzoic acid in 80 ml of methylene chloride was stirred at 23° C. for 4 days and then at 40° C. for 16 h. The mixture was then extracted with 100 ml of 10% strength aqueous sodium bisulfate solution, with 100 ml of a 10% strength aqueous sodium bicarbonate solution and three times with 80 ml of water each time. The organic phase was concentrated, and the residue was chromatographed on silica gel with cyclohexane/ethyl acetate (5:1). Yield: 3.6 g (76%) of colorless crystals; melting point: 156°-157° C.

Workup

  1. extractionThe mixture was then extracted with 100 ml of 10% strength aqueous sodium bisulfate solution, with 100 ml of a 10% strength aqueous sodium bicarbonate solution and three times with 80 ml of water each time
  2. concentrationThe organic phase was concentrated
  3. customthe residue was chromatographed on silica gel with cyclohexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-01c17aa6560347d0ba331bb0edb3aec0
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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