m-Chloroperbenzoic acid → HCID 22621214, compound

HRID 841159Notes

Reaction equation

HRID 841159 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[Cl:12][C:13]1[C:14]([N:31]([CH2:36][CH3:37])[C:32]([O:34][CH3:35])=[O:33])=[C:15]([CH:26]=[CH:27][C:28]=1SC)[C:16]([C:18]1[CH:19]=[N:20][O:21][C:22]=1[CH:23]1[CH2:25][CH2:24]1)=[O:17].[S:38](S([O-])=O)([O-:41])(=O)=[O:39].[Na+].[Na+]>ClCCl>[Cl:12][C:13]1[C:14]([N:31]([CH2:36][CH3:37])[C:32]([O:34][CH3:35])=[O:33])=[C:15]([CH:26]=[CH:27][C:28]=1[S:38]([CH3:2])(=[O:41])=[O:39])[C:16]([C:18]1[CH:19]=[N:20][O:21][C:22]=1[CH:23]1[CH2:24][CH2:25]1)=[O:17]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 22621077HCID 22621077, compound2×

Product 1

HCID 22621214HCID 22621214, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (1.81 g of a 50% oil dispersion) was added to a stirred solution of 4-[3-chloro-2-(N-ethyl-N-methoxycarbonylamino)-4-(methylthio)benzoyl]-5-cyclopropyl-isoxazole (compound 35, 0.92 g) in dichloromethane. After 5 hours, a solution of sodium metabisulphite was added and the mixture stirred for 5 minutes. The organic phase was washed with sodium bicarbonate solution and water, dried (anhydrous magnesium sulphate) and evaporated. The residue was triturated (with a hexane/ether solution) to yield 4-[3-chloro-2-(N-ethyl-N-methoxycarbonylamino)-4-methylsulphonylbenzoyl]-5-cyclopropylisoxazole (compound number 48, 0.95 g) as a white solid, m.p. 152-155.5° C.

Workup

  1. washThe organic phase was washed with sodium bicarbonate solution and water
  2. dry with materialdried (anhydrous magnesium sulphate)
  3. customevaporated
  4. customThe residue was triturated (with a hexane/ether solution)

Sources & evidence

ORD record
ord-5db34629a26840eb9ae93bf048b9f676
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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