m-Chloroperbenzoic acid → HCID 21696678, compound

HRID 378806Notes

Reaction equation

HRID 378806 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([S:9][CH3:10])[C:5]=2[C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][C:13]=2[CH3:22])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([S:9]([CH3:10])=[O:32])[C:5]=2[C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:19])=[O:20])=[CH:14][C:13]=2[CH3:22])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21696680HCID 21696680, compound

Product 1

HCID 21696678HCID 21696678, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-cyclopropyl-3-methylthio-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole (750 mg, 2.127 mmol) in dichloromethane (35 mL) was added 3-chloroperbenzoic acid (650 mg, 57-87%, Aldrich). The resulting mixture was stirred at r.t. for 2 hours, then diluted with dichloromethane, washed with aqueous sodium bicarbonate, brine, dried and evaporated to dryness. The crude product was purified by preparative thin-layer chromatography to give crystalline 5-cyclopropyl-3-methylsulfinyl-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole (436 mg), rp. 147° C. and 5-cyclopropyl-3-methylsulfonyl-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole (378 mg), m.p. 142° C.

Workup

  1. washwashed with aqueous sodium bicarbonate, brine
  2. customdried
  3. customevaporated to dryness
  4. customThe crude product was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-a43b711a09a8455b9a6268fa52efdd5c
Source dataset
uspto-grants-2001_10
Patent number
US06297198B1

Reaction notes

Loading…