m-Chloroperbenzoic acid → HCID 54332068, compound

HRID 2393036Notes

Reaction equation

HRID 2393036 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:28]=[C:27]([S:29][CH3:30])[CH:26]=[CH:25][C:14]=1[C:15]([C:17]1[CH:18]=[N:19][O:20][C:21]=1[CH:22]1[CH2:24][CH2:23]1)=[O:16].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl>[Cl:12][C:13]1[CH:28]=[C:27]([S:29]([CH3:30])=[O:9])[CH:26]=[CH:25][C:14]=1[C:15]([C:17]1[CH:18]=[N:19][O:20][C:21]=1[CH:22]1[CH2:24][CH2:23]1)=[O:16]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 656671Sodium PyrosulfiteHCID 54015502HCID 54015502, compound

Product 1

HCID 54332068HCID 54332068, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

3-Chloroperbenzoic acid (1.3 g) was added to a solution of 4-[2-chloro-4-(methylsulphenyl)benzoyl]-5-cyclopropylisoxazole (2.0 g) in dichloromethane whilst maintaining the temperature below -15° C. The mixture was stirred at -15° C. for 2 hours and allowed to warm to room temperature. The mixture was stirred for 2 hours and then recooled to -15° C. 3-Chloroperbenzoic acid (0.7 g) was added and the mixture was stirred at -15° C. for 1 hour and at room temperature for 1 hour. A solution of sodium metabisulphite was added. The organic layer was washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica eluted with ethyl acetate and hexane (3:2) to give 4-[2-chloro-4-(methylsulphinyl)benzoyl]-5-cyclopropylisoxazole (1.3 g) as a white solid, m.p.117° C.

Workup

  1. temperaturewhilst maintaining the temperature below -15° C
  2. temperatureto warm to room temperature
  3. stirringThe mixture was stirred for 2 hours
  4. customrecooled to -15° C
  5. stirringthe mixture was stirred at -15° C. for 1 hour and at room temperature for 1 hour
  6. washThe organic layer was washed with water
  7. dry with materialdried (magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by column chromatography on silica
  11. washeluted with ethyl acetate and hexane (3:2)

Sources & evidence

ORD record
ord-9adf54a68edb4682a354cb83871b0cc9
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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