m-Chloroperbenzoic acid → HCID 18977935, compound

HRID 2393042Notes

Reaction equation

HRID 2393042 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[CH:12]1([C:15]2[O:19][N:18]=[CH:17][C:16]=2[C:20](=[O:30])[C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[C:23](SC)[CH:22]=2)[CH2:14][CH2:13]1.[S:31](S([O-])=O)([O-:34])(=O)=[O:32].[Na+].[Na+]>ClCCl>[CH:12]1([C:15]2[O:19][N:18]=[CH:17][C:16]=2[C:20](=[O:30])[C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[C:25]([S:31]([CH3:2])(=[O:34])=[O:32])[CH:26]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 18977973HCID 18977973, compound

Product 1

HCID 18977935HCID 18977935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (about 50%, 2.5 g) was added to a solution of 5-cyclopropyl-4-(4-methyl-3-methylsulphenylbenzoyl)isoxazole (0.8 g) in dichloromethane and the mixture was stirred at room temperature overnight. An aqueous solution of sodium metabisulphite was added and the mixture was stirred for 20 minutes. The solid was filtered and the filtrate layers separated. The organic phase was washed with aqueous sodium acetate, brine, dried and filtered. The filtrate was evaporated and the residue triturated with ether and filtered to give 5-cyclopropyl-4-(4-methyl-3-methylsulphonylbenzoyl)isoxazole (0.65 g) as a white solid, m.p. 126.4°-127.7° C.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. filtrationThe solid was filtered
  3. customthe filtrate layers separated
  4. washThe organic phase was washed with aqueous sodium acetate, brine
  5. customdried
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customthe residue triturated with ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-43a98d7b87bf43959bcc749d85ca0258
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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