Sodium Thiosulfate → HCID 21829904, compound

HRID 1600548Notes

Reaction equation

HRID 1600548 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:26])[C:11]([N:14]1[C:18](=[O:19])[CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)S[CH2:15]1)([CH3:13])[CH3:12].ClC1C=CC=C(C(OO)=O)C=1.[S:38]([O-:42])([O-])(=[O:40])=S.[Na+].[Na+]>ClCCl.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:26])[C:11]([N:14]1[C:18](=[O:19])[CH:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:38](=[O:42])(=[O:40])[CH2:15]1)([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 21829909HCID 21829909, compound

Product 1

HCID 21829904HCID 21829904, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,5-difluorophenyl)-2-(5-phenylthiazolidin-4-on-3-yl)isobutyramide (1.3 g) prepared according to Example 13 in dichloromethane (25 mL) was added portionwise 70% m-chloroperbenzoic acid (1 g) under ice-cooling, and the mixture was stirred for 30 minutes at room temperature. After adding a small amount of sodium thiosulfate, the mixture was diluted with chloroform and washed with a saturated sodium hydrogencarbonate aqueous solution. After distilling off the solvent under reduced pressure, the resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=3/1) to give crystals, which were washed with a mixture of isopropyl ether-ethanol (10:1) to give 0.26 g of the title compound as crystals.

Workup

  1. temperaturecooling
  2. washwashed with a saturated sodium hydrogencarbonate aqueous solution
  3. distillationAfter distilling off the solvent under reduced pressure
  4. customthe resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=3/1)
  5. customto give crystals, which
  6. washwere washed with a mixture of isopropyl ether-ethanol (10:1)

Sources & evidence

ORD record
ord-c3be5a6a9f7b4920bec871e8243c955f
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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