m-Chloroperbenzoic acid → HCID 18996926, compound

HRID 374413Notes

Reaction equation

HRID 374413 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]([C:22]2[C:23]([S:28][CH3:29])=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH2:14][CH2:13]1>ClCCl>[CH:12]1([C:15]2[O:19][N:18]=[CH:17][C:16]=2[C:20]([C:22]2[C:23]([S:28]([CH3:29])=[O:6])=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18996915HCID 18996915, compound

Product 1

HCID 18996926HCID 18996926, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

3-Chloroperoxybenzoic acid, an oxidant (2.85 g), was added to a stirred solution of 5-cyclopropyl-4-(2-methylsulphenylpyridin-3-oyl)isoxazole (236 g) in dichloromethane at -20° C. A further quantity of the oxidant (0.14 g) was added after 5 minutes. The reaction mixture was stirred at -20° C. until analysis (by thin layer chromatography) indicated reaction was complete. The mixture was filtered and the filtrate was washed successively with aqueous sodium bicarbonate solution and aqueous sodium metabisulphite solution, dried (anhydrous magnesium sulphate), filtered and evaporated. The crude product was suspended in refluxing acetonitrile. The suspension was cooled to room temperature and filtered. The product was dried to yield 5-cyclopropyl-4-(2-methylsulphinylpyridin-3-oyl)isoxazole (compound 7, 2.0 g) as colourless crystals, m.p.148°-152.4° C.

Workup

  1. additionA further quantity of the oxidant (0.14 g) was added after 5 minutes
  2. customreaction
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed successively with aqueous sodium bicarbonate solution and aqueous sodium metabisulphite solution
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated
  8. temperaturein refluxing acetonitrile
  9. temperatureThe suspension was cooled to room temperature
  10. filtrationfiltered
  11. customThe product was dried

Sources & evidence

ORD record
ord-2a6df04fd20a4b2c86e48999006df682
Source dataset
uspto-grants-1996_01
Patent number
US05480857

Reaction notes

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