Hydrogen Peroxide → 3-(1-Methyl-1,2,3,4-tetrazol-5-yl)sulfinylpropyl 2-pyridyl sulfoxide

HRID 1758334

Reaction equation

HRID 1758334 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([CH2:9][CH2:10][CH2:11][S:12][C:13]1[N:17]([CH3:18])[N:16]=[N:15][N:14]=1)=[O:8].OO.S([O-])(O)=[O:22].[Na+].C(OO)=O>C(O)=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([CH2:9][CH2:10][CH2:11][S:12]([C:13]1[N:17]([CH3:18])[N:16]=[N:15][N:14]=1)=[O:22])=[O:8]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 66051Performic AcidHCID 3061976Pyridine, 2-((3-((1-methyl-1H-tetrazol-5-yl)thio)propyl)sulfinyl)-HCID 23665763Sodium Bisulfite

Product 1

HCID 130619833-(1-Methyl-1,2,3,4-tetrazol-5-yl)sulfinylpropyl 2-pyridyl sulfoxide

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

3-(1-Methyl-1,2,3,4-tetrazol-5-yl)thiopropyl 2-pyridyl sulfoxide (2.8 g) is dissolved in formic acid (20 ml) and thereto is added with stirring 30% hydrogen peroxide (1.3 g) at room temperature, and the mixture is stirred for 5 hours. To the mixture is added sodium hydrogen sulfite under ice-cooling in order to decompose excess performic acid. Water is added to the resulting mixture and it is extracted with chloroform. The chloroform solution is washed with water and saturated aqueous sodium bicarbonate and dried over magnesium sulfate. After chloroform is distilled off, the residue is purified by column chromatography [Wakogel C-200, eluting agent, chloroform-methanol (50:1)] to give 3-(1-methyl-1,2,3,4-tetrazol-5-yl)sulfinylpropyl 2-pyridyl sulfoxide (0.8 g) as colorless liquid, nD28.5 =1.5795.

Workup

  1. additionis added
  2. temperaturecooling in order
  3. extractionis extracted with chloroform
  4. washThe chloroform solution is washed with water and saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter chloroform is distilled off
  7. customthe residue is purified by column chromatography [Wakogel C-200, eluting agent, chloroform-methanol (50:1)]

Sources & evidence

ORD record
ord-24220bbc8e6a4f76acef5842d8956398
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Linked notes

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