Sodium Thiosulfate → HCID 3013410, compound

HRID 565955Notes

Reaction equation

HRID 565955 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 (200mg) in tetrahydrofuran (10ml) was added 3-chloro-perbenzoic acid (70%, 0.18g) 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) (124mg) 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-9905d4ab00b644d7b57e2665023355bf
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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