m-Chloroperbenzoic acid → HCID 19871317, compound

HRID 329652Notes

Reaction equation

HRID 329652 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([O:5][C:6]1[CH:10]=[C:9]([CH2:11][S:12][CH3:13])[O:8][N:7]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH3:1][N:2]([CH3:14])[C:3]([O:5][C:6]1[CH:10]=[C:9]([CH2:11][S:12]([CH3:13])=[O:23])[O:8][N:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19871333HCID 19871333, compound

Product 1

HCID 19871317HCID 19871317, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 757 mg of 3-dimethylcarbamoyloxy-5-methylthiomethylisoxazole in 5 ml of methylene chloride was added dropwise over a period of 30 minutes, with stirring, to an ice-cooled solution of 711 mg of m-chloroperbenzoic acid in 15 ml of methylene chloride. The mixture was then stirred for a further 30 minutes, after which it was filtered and the precipitate was washed with 2 ml of methylene chloride. The filtrate and the washings were combined, and then the solvent was removed by distillation, leaving a colourless, crystalline residue, which was recrystallized from diethyl ether, to give 700 mg (yield 86.1%) of 3-dimethylcarbamoyloxy-5-methylsulphinylmethylisoxazole, in the form of colourless needles melting at 84°-85° C.

Workup

  1. filtrationafter which it was filtered
  2. washthe precipitate was washed with 2 ml of methylene chloride
  3. customthe solvent was removed by distillation
  4. customleaving a colourless, crystalline residue, which
  5. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-29442d0c7a3b4b2d82230c472444acfe
Source dataset
uspto-grants-1990_01
Patent number
US04892882

Reaction notes

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