m-Chloroperbenzoic acid → HCID 13271697, compound

HRID 1380065Notes

Reaction equation

HRID 1380065 reaction equation
[Cl:1][C:2]1[C:3](=[O:16])[N:4]([C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[O:5][C:6]=1[CH2:7][S:8]([CH3:10])=[O:9].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:3](=[O:16])[N:4]([C:11](=[O:15])[N:12]([CH3:13])[CH3:14])[O:5][C:6]=1[CH2:7][S:8]([CH3:10])(=[O:25])=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13271695HCID 13271695, compound

Product 1

HCID 13271697HCID 13271697, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

363 mg of 4-chloro-2-dimethylcarbamoyl-5-methylsulphinylmethyl-4-isoxazolin-3-one were dissolved in 20 ml of methylene chloride, and then 300 mg of crystals of m-chloroperbenzoic acid were added little by little, whilst ice-cooling and stirring. The mixture was allowed to stand overnight at room temperature, and was then washed, in turn, with 20 ml of a 5% w/v aqueous solution of sodium hydrogen carbonate and then twice, each time with 20 ml of water. The washings were combined and then extracted twice, each time with 10 ml of chloroform. The organic phases were combined and dried over anhydrous sodium sulphate, after which the solvent was distilled off. The residue was recrystallized from a mixture of methylene chloride and diisopropyl ether, to give 337 mg (yield 87.5% of theory) of the title compound in the form of crystals melting at 129°-129.5° C.

Workup

  1. temperaturecooling
  2. washwas then washed, in turn, with 20 ml of a 5% w/v aqueous solution of sodium hydrogen carbonate
  3. extractionextracted twice
  4. dry with materialdried over anhydrous sodium sulphate
  5. distillationafter which the solvent was distilled off
  6. customThe residue was recrystallized from a mixture of methylene chloride and diisopropyl ether

Sources & evidence

ORD record
ord-43ff54861c8741d1b0052f40c8914843
Source dataset
uspto-grants-1986_04
Patent number
US04579860

Reaction notes

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