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

HRID 1277109Notes

Reaction equation

HRID 1277109 reaction equation
[CH:1]1([S:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]3[CH2:20][CH2:21][O:22][C:23]4[CH:29]=[CH:28][C:27]([C:30]5[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=5)=[CH:26][C:24]=4[CH:25]=3)=[O:18])=[CH:12][CH:11]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:45])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH:1]1([S:7]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([C:19]3[CH2:20][CH2:21][O:22][C:23]4[CH:29]=[CH:28][C:27]([C:30]5[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=5)=[CH:26][C:24]=4[CH:25]=3)=[O:18])=[CH:14][CH:15]=2)(=[O:45])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 54132653N-(4-(cyclohexylsulfinylmethyl)phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

HCID 18472638N-(4-(cyclohexylsulfonylmethyl)phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-(4-(cyclohexylsulfinylmethyl)phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.13 g) in chloroform (45 ml) was added 70% m-chloroperbenzoic acid (mCPBA) (0.097 g) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To the mixture was added sodium thiosulfate solution, and the mixture was washed with sodium hydrogen carbonate solution and water, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give crude crystals, which were recrystallized from ethanol-hexane to give N-(4-(cyclohexylsulfonylmethyl)phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 107) (0.11 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with sodium hydrogen carbonate solution and water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customUnder reduced pressure, the solvent was evaporated
  5. customto give crude crystals, which
  6. customwere recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-fce5e016fcd94952982c4f603b8d7c88
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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