Hydrogen Peroxide → HCID 20509852, compound

HRID 1758287Notes

Reaction equation

HRID 1758287 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.OO.[OH2:14].S([O-])(O)=[O:16].[Na+]>C(O)=O>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:16])=[O:14]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 20509836HCID 20509836, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 20509852HCID 20509852, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2-(3-Chloropropyl)thiopyridine (3.7 g) prepared in Reference Example 3 is dissolved in formic acid (30 ml). 30% Aqueous hydrogen peroxide (6.9 g) is added to the solution and the mixture is stirred at room temperature for 4 hours. After dilution with water, sodium hydrogen sulfite is added to the mixture with ice-cooling to destroy excess formic acid. The mixture is extracted with chloroform and the extract is washed with water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride and dried over magnesium sulfate. Chloroform is distilled off and the residue is purified by column chromatography (Kieselgel 60). The column is eluted with chloroform-methanol (50:1) to obtain 2-pyridyl 3-chloropropyl sulfone (4 g) as colorless liquid.

Workup

  1. temperaturecooling
  2. customto destroy excess formic acid
  3. extractionThe mixture is extracted with chloroform
  4. washthe extract is washed with water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationChloroform is distilled off
  7. customthe residue is purified by column chromatography (Kieselgel 60)
  8. washThe column is eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-0ed274e13b1243d2a9217dc79d47c58f
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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