Chloroform → 2-(2-Chloro-1-oxido-4-pyridinyl)-5-(trifluoromethyl)benzoxazole

HRID 1913608Notes

Reaction equation

HRID 1913608 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:4][N:3]=1.C(Cl)(Cl)Cl.ClC1C=CC=C(C(OO)=[O:33])C=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:4][N+:3]=1[O-:33]

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 70297m-Chloroperbenzoic acid2×HCID 72942539HCID 72942539, compound

Product 1

HCID 866510392-(2-Chloro-1-oxido-4-pyridinyl)-5-(trifluoromethyl)benzoxazoleYield 90.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 0.40 g of 2-(2-chloropyridin-4-yl)-5-(trifluoromethyl)benzoxazole and 4 ml of chloroform, 0.53 g of 65% m-chloroperbenzoic acid was added while ice-cooling. The reaction mixture was stirred while ice-cooling for 30 minutes, then stirred at room temperature for three hours, and then stirred while heating at 50° C. for 1.5 hours. To the mixture, 0.53 g of 65% m-chloroperbenzoic acid and 2 ml of chloroform were added and stirred while heating at 60° C. for five hours. The reaction mixture was cooled to room temperature, then diluted with ethyl acetate, and washed with 5% aqueous solution of sodium hydroxide and a saturated sodium chloride solution, sequentially. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 0.38 g of 2-chloro-4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridine N-oxide (hereinafter, referred to as “active compound 22”).

Workup

  1. additionwas added while ice-
  2. temperaturecooling
  3. temperaturecooling for 30 minutes
  4. stirringstirred at room temperature for three hours
  5. stirringstirred
  6. stirringstirred
  7. temperaturewhile heating at 60° C. for five hours
  8. temperatureThe reaction mixture was cooled to room temperature
  9. washwashed with 5% aqueous solution of sodium hydroxide
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-783b5b5dde694e6b8ada3c573b49baae
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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