m-Chloroperbenzoic acid → HCID 54417279, compound

HRID 266503Notes

Reaction equation

HRID 266503 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:31])[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[C:22]=2[S:29][CH3:30])[CH2:14][CH2:13]1>ClCCl>[CH:12]1([C:15]2[O:19][N:18]=[CH:17][C:16]=2[C:20](=[O:31])[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[C:22]=2[S:29]([CH3:30])=[O:6])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15452216HCID 15452216, compound

Product 1

HCID 54417279HCID 54417279, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

3-Chloroperoxybenzoic acid (2.0 g) was added to a solution of 5-cyclopropyl-4-(3,4-dichloro-2-methylsulphenylbenzoyl)isoxazole (1.86 g) in dichloromethane while maintaining the temperature around -15° C. The mixture was stirred at -15° C. for 1 hour and at room temperature for 1 hour. It was recooled to -15° C. and filtered. The filtrate was evaporated to dryness and the residue was purified by dry column flash chromatography eluted with a mixture of ethyl acetate and n-hexane. The product was recrystallized from a mixture of ethyl acetate and n-hexane to give 5-cyclopropyl-4-(3,4-dichloro-2-methylsulphinylbenzoyl)isoxazole (compound 285, 0.3 g) as a white solid, m.p. 110°-112° C.

Workup

  1. customwas recooled to -15° C.
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified
  5. customby dry column flash chromatography
  6. washeluted with a mixture of ethyl acetate and n-hexane
  7. customThe product was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-02bdeaf213ba498b89239e8bfe065314
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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