Sodium Thiosulfate → HCID 21995921, compound

HRID 1978566Notes

Reaction equation

HRID 1978566 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]3S[CH2:17][CH2:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][C:13]=3[CH:23]=2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=O)C=1.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]3[S:35](=[O:39])(=[O:37])[CH2:17][CH2:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][C:13]=3[CH:23]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 18472336Methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 21995921HCID 21995921, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (0.60 g) in THF (10 ml) was added at 0° C. 70% 3-chloroperbenzoic acid (1.0 g), and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. To the mixture was added an aqueous solution of sodium thiosulfate, and the mixture was stirred for a few minutes and extracted with dichloromethane. The organic layer was washed with sodium bicarbonate solution and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give solid, which was recrystallized from ethyl acetate/hexane to give colorless crystals of methyl 7-(4-methoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (584.5 mg).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with sodium bicarbonate solution and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give solid, which
  6. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b816564710ea49218c195289edd4cdad
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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