Sodium Thiosulfate → HCID 21995797, compound

HRID 1978600Notes

Reaction equation

HRID 1978600 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3S[CH2:16][CH2:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][C:12]=3[CH:22]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[S:34]([O-:38])([O-])(=[O:36])=S.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:34](=[O:38])(=[O:36])[CH2:16][CH2:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][C:12]=3[CH:22]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 21995657HCID 21995657, compound

Product 1

HCID 21995797HCID 21995797, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 7-(4-methylphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (1.5 g) in dichloromethane (25 ml) was added, under ice-cooling, 70% mCPBA (2.4 g), and the mixture was stirred at room temperature for 1 hour. To the solution was added an aqueous solution of sodium thiosulfate, and the mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with sodium hydrogen carbonate solution, water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give methyl 7-(4-methylphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (1.6 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. concentrationthe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-30c98e7beec84c119a1dec4adedf49c3
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

Loading…