Sodium Thiosulfate → HCID 18472310, compound

HRID 2228153Notes

Reaction equation

HRID 2228153 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]3[CH2:22][CH2:23][O:24][C:25]4[CH:31]=[CH:30][C:29]([C:32]5[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=5)=[CH:28][C:26]=4[CH:27]=3)=[O:20])=[CH:14][CH:13]=2)=[N:7][CH:8]=[CH:9][CH:10]=1.ClC1C=CC=C(C(OO)=[O:47])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[O-:47][N+:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:6]=1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([C:21]2[CH2:22][CH2:23][O:24][C:25]3[CH:31]=[CH:30][C:29]([C:32]4[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=4)=[CH:28][C:26]=3[CH:27]=2)=[O:20])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 18472482HCID 18472482, compound

Product 1

HCID 18472310HCID 18472310, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4—(3-methoxymethoxypyridin-2-ylmethyl)phenyl]-7—(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (300 mg) in tetrahydrofuran (10 ml) was added 3-chloroperbenzoic acid (70%, 0.22 g) at 0° C., and the mixture was stirred at room temperature for 18 hours. To the mixture was added sodium thiosulfate, and the mixture was stirred for a few minutes. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:15→1:10), and recrystallized from ethanol to give N-[4—(1-oxido-3-methoxymethoxypyridin-2-ylmethyl)phenyl]-7—(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 173) (203 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 under reduced pressure
  6. customThe residue was separated
  7. custompurified with column chromatography (ethanol/ethyl acetate=1:15→1:10)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3c43c7bb94e14434884842beee1202aa
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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