Sodium Thiosulfate → 7-(4-methylphenyl)-N-(4-(phenylsulfinylmethyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

HRID 565934Notes

Reaction equation

HRID 565934 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][S:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:23][CH:22]=4)=[O:19])=[CH:13][C:12]=3[CH:35]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:44])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][S:28]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)=[O:44])=[CH:23][CH:22]=4)=[O:19])=[CH:13][C:12]=3[CH:35]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 184725617-(4-methylphenyl)-N-(4-(phenylthiomethyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

HCID 539283207-(4-methylphenyl)-N-(4-(phenylsulfinylmethyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamideYield 106.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(4-methylphenyl)-N-(4-(phenylthiomethyl)-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.1g) in dichloromethane (30ml) was added 70% m-chloroperbenzoic acid (0.046g) at the temperature ranging from −20 to −10° C., and the mixture was stirred for 30 minutes. To the mixture was added sodium thiosulfate solution, and the mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with sodium hydrogen carbonate solution, water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 7-(4-methylphenyl)-N-(4-(phenylsulfinylmethyl)-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 108) (0.11g) as colorless crystals.

Workup

  1. customranging from −20 to −10° C.
  2. concentrationthe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customto give crude crystals, which
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ecba26b36b1f45dc8654c5817396a45b
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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