Sodium Thiosulfate → Pyridine, 4-phenoxy-, 1-oxide

HRID 2080043Notes

Reaction equation

HRID 2080043 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:22])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[O:1]([C:8]1[CH:13]=[CH:12][N+:11]([O-:22])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 2496514-PhenoxypyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 520629Pyridine, 4-phenoxy-, 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenoxypyridine (3.0 g, 17.5 mmol) in dichloromethane (500 mL) was added 3-chloro-perbenzoic acid (5.18 g, 21.0 mmol) on an ice bath, and the solution was stirred for 22 hours. An aqueous solution of saturated sodium thiosulfate and an aqueous solution of saturated sodium bicarbonate were added to the reaction solution, the solution was stirred at room temperature for 10 minutes, then, the organic layer was separated, washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and 4-phenoxy-pyridine N-oxide (3.3 g, quantitatively) was obtained as a pale yellow solid.

Workup

  1. stirringthe solution was stirred at room temperature for 10 minutes
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-64db1afa3a4242659f9fef79c2445101
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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