m-Chloroperbenzoic acid → 2-(1-Oxido-4-pyridinyl)-5-(trifluoromethyl)benzoxazole

HRID 1913600Notes

Reaction equation

HRID 1913600 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:9]2[O:8][C:7]([C:4]3[CH:5]=[CH:6][N+:1]([O-:28])=[CH:2][CH:3]=3)=[N:11][C:10]=2[CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66879735HCID 66879735, compound

Product 1

HCID 668798622-(1-Oxido-4-pyridinyl)-5-(trifluoromethyl)benzoxazoleYield 78.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 0.47 g of 2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole and 5 ml of chloroform, 0.64 g of 65% m-chloroperbenzoic acid was added while ice-cooling. The reaction mixture was stirred while ice-cooling for 30 minutes, and then stirred at room temperature for 1.5 hours. The reaction mixture was diluted with chloroform, and washed with 5% aqueous solution of sodium hydroxide and a saturated sodium chloride solution. Organic layers were dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 0.39 g of 4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridine N-oxide (hereinafter, referred to as “active compound 14”).

Workup

  1. additionwas added while ice-
  2. temperaturecooling
  3. temperaturecooling for 30 minutes
  4. stirringstirred at room temperature for 1.5 hours
  5. washwashed with 5% aqueous solution of sodium hydroxide
  6. dry with materialOrganic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f55cdcc84fda4c7db34f86f7d2e0e424
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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