Hydrogen Peroxide → 3-(1-Methyl-1,2,3,4-tetrazol-5-yl)sulfinylpropyl 2-pyridyl sulfoxide
Reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:5][N:4]=[N:3]1.OO.S([O-])(O)=[O:21].[Na+].C(OO)=O.[OH2:29]>C(O)=O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:11]([CH2:10][CH2:9][CH2:8][S:7]([C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1)=[O:21])=[O:29]Participants
Procedure
1-Methyl-5-[3-(2-pyridyl)thiopropyl]thio-1,2,3,4-tetrazole (2.2 g) is dissolved in formic acid (20 ml), and thereto is added with stirring 30% hydrogen peroxide (2.2 g) at room temperature. The mixture is stirred at room temperature for 5 hours, and thereto is added sodium hydrogensulfite under ice-cooling in order to decompose excess amount of performic acid. Water is added to the mixture and the mixture 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 [Kieselgel 60, eluting agent, chloroform-methanol (50:1)] to give 3-(1-methyl-1,2,3,4-tetrazol-5-yl)sulfinylpropyl 2-pyridyl sulfoxide (0.5 g) as colorless liquid, nD28.5 =1.5795
Workup
- additionis added
- temperaturecooling in order
- extractionthe mixture is extracted with chloroform
- washThe chloroform solution is washed with water and saturated aqueous sodium bicarbonate
- dry with materialdried over magnesium sulfate
- distillationAfter chloroform is distilled off
- customthe residue is purified by column chromatography [Kieselgel 60, eluting agent, chloroform-methanol (50:1)]
Sources & evidence
- ORD record
- ord-bcd70a9f1ee143188c16d905b8f5ac1f
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04372953
Reaction notes
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