Sodium Thiosulfate → HCID 3013410, compound

HRID 1277132Notes

Reaction equation

HRID 1277132 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH2:18][CH2:19][O:20][C:21]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)=[CH:24][C:22]=3[CH:23]=2)=[O:16])=[CH:10][CH:9]=1.ClC1C=CC=C(C(OO)=[O:43])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[O-:43][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH2:18][CH2:19][O:20][C:21]3[CH:27]=[CH:26][C:25]([C:28]4[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=4)=[CH:24][C:22]=3[CH:23]=2)=[O:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11166749HCID 11166749, compound

Product 1

HCID 3013410HCID 3013410, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(2-pyridylmethyl)phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (200 mg) in tetrahydrofuran (10 ml) was added 3-chloro-perbenzoic acid (70%, 0.18 g) at 0° C., and the mixture was stirred at room temperature for 17 hours. To the reaction mixture was added sodium thio-sulfate solution, and the mixture was stirred for a few minutes. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried with magnesium sulfate and concentrated to give crystals, which were collected by filtration and was recrystallized from ethanol to give N-[4-(1-oxidopyridin-2-ylmethyl)phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 162) (124 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred for a few minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customto give crystals, which
  7. filtrationwere collected by filtration
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-b7042ee6fffa4ac49ec566b58484396b
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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