m-Chloroperbenzoic acid → HCID 18989201, compound

HRID 2395548Notes

Reaction equation

HRID 2395548 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9]([C:11]2[C:19]3[O:18][C:17]([F:21])([F:20])[O:16][C:15]=3[C:14](SC)=[CH:13][CH:12]=2)=[O:10])[CH2:3][CH2:2]1.Cl[C:25]1C=CC=C(C(OO)=O)C=1.[S:35](S([O-])=O)([O-:38])(=O)=[O:36].[Na+].[Na+]>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9]([C:11]2[C:19]3[O:18][C:17]([F:21])([F:20])[O:16][C:15]=3[C:14]([S:35]([CH3:25])(=[O:38])=[O:36])=[CH:13][CH:12]=2)=[O:10])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 18989225HCID 18989225, compound

Product 1

HCID 18989201HCID 18989201, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
1 °C

Procedure

A solution of 5-cyclopropyl-4-(2,2-difluoro-7-methylsulphenyl-1,3-benzodioxol-4-oyl)isoxazole (0.64 g) in dichloromethane was treated with m-chloroperbenzoic acid (55%, 1.5 g). After 2 hours the mixture was cooled to 1° C., and 1M sodium metabisulphite solution added. The filtered solution was separated and the organic phase washed with sodium acetate solution, brine, dried over anhydrous sodium sulphate and evaporated to give 5-cyclopropyl-4-(2,2-difluoro-7-methylsulphonyl-1,3-benzodioxol-4-oyl)isoxazole (compound 5, 0.35 g) as a white solid, m.p. 164°-165° C.

Workup

  1. customThe filtered solution was separated
  2. washthe organic phase washed with sodium acetate solution, brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-e4c26b0a77e549dc9b5088e266ea42e0
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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