Hydrogen Peroxide → HCID 20509824, compound

HRID 1758286Notes

Reaction equation

HRID 1758286 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.[OH:12]O>C(O)=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:12]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 20509836HCID 20509836, compound

Product 1

HCID 20509824HCID 20509824, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

2-(3-Chloropropyl)thiopyridine (4.4 g) prepared in Reference Example 3 is dissolved in formic acid (40 ml). 30% Aqueous hydrogen peroxide (2.7 g) is added to the solution and the mixture is stirred at room temperature for 3 hours. The mixture is allowed to stand at room temperature for overnight, diluted with water and extracted with chloroform. The chloroform solution 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 sulfoxide (2.7 g) as colorless liquid.

Workup

  1. waitto stand at room temperature for overnight
  2. extractionextracted with chloroform
  3. washThe chloroform solution is washed with water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationChloroform is distilled off
  6. customthe residue is purified by column chromatography (Kieselgel 60)
  7. washThe column is eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-df98d855c9804286a691323f461782dd
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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