Sodium Thiosulfate → HCID 18472656, compound

HRID 1387887Notes

Reaction equation

HRID 1387887 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH2:17][CH2:18][O:19][C:20]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=5)=[CH:23][C:21]=4[CH:22]=3)=[O:15])=[CH:9][CH:8]=2)[CH:2]=1.ClC1C=CC=C(C(OO)=[O:42])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[O-:42][N+:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH2:17][CH2:18][O:19][C:20]4[CH:26]=[CH:25][C:24]([C:27]5[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=5)=[CH:23][C:21]=4[CH:22]=3)=[O:15])=[CH:9][CH:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 18472449HCID 18472449, compound

Product 1

HCID 18472656HCID 18472656, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(3-pyridyl)phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (400 mg) in tetrahydrofuran (50 ml) was added 3-chloro-perbenzoic acid (70%, 0.34 g) at 0° C., and the mixture was stirred at room temperature for 68 hours. To the reaction mixture was added sodium thiosulfate solution, and the mixture was stirred for a few minutes and extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:1), and recrystallized from ethanol-chloroform to give N-[4-(1-oxidopyridin-3-yl)phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 165) (216 mg) as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred for a few minutes
  2. extractionextracted with dichloromethane
  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. customThe residue was separated
  7. custompurified with column chromatography (ethanol/ethyl acetate=1:1)
  8. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-200fe183ef6149578020c998ac2f307e
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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