m-Chloroperbenzoic acid → HCID 54443052, compound

HRID 266501Notes

Reaction equation

HRID 266501 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH:12]1([C:15]2[O:19][N:18]=[CH:17][C:16]=2[C:20](=[O:33])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[S:31][CH3:32])[CH2:14][CH2:13]1>ClCCl>[CH:12]1([C:15]2[O:19][N:18]=[CH:17][C:16]=2[C:20](=[O:33])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][C:22]=2[S:31]([CH3:32])=[O:6])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 11404656HCID 11404656, compound

Product 1

HCID 54443052HCID 54443052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

3-Chloroperoxybenzoic acid (0.95 g) was added to a cooled solution of 5-cyclopropyl-4-(2-methylsulphenyl-4-trifluoromethylbenzoyl)isoxazole (1.2 g) in dichloromethane with stirring at -20° C. The mixture was stirred at -20° C. for 2 hours and allowed to warm slowly to 0° C. It was stirred for 1 hour and recooled to -20° C. 3-Chloroperoxybenzoic acid (0.4 g) was added at -20° C. and the mixture was allowed to warm slowly to 0° C and stirred for 1 hour. The mixture was then filtered and the filtrate was washed with water, aqueous sodium metabisulphite solution, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ethyl acetate and filtered to give 5-cyclopropyl-4-(2-methylsulphinyl-4-trifluoromethylbenzoyl)isoxazole, compound 264 (0.59 g) as a white solid, m.p. 149°-151° C.

Workup

  1. stirringThe mixture was stirred at -20° C. for 2 hours
  2. temperatureto warm slowly to 0° C
  3. stirringIt was stirred for 1 hour
  4. customrecooled to -20° C
  5. temperatureto warm slowly to 0° C
  6. stirringstirred for 1 hour
  7. filtrationThe mixture was then filtered
  8. washthe filtrate was washed with water, aqueous sodium metabisulphite solution
  9. dry with materialdried (anhydrous magnesium sulphate)
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness
  12. customthe residue was triturated with ethyl acetate
  13. filtrationfiltered

Sources & evidence

ORD record
ord-62bbe96d74014c1e8d94e671e40c74a2
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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