Potassium Carbonate → 1-Methyl-5-(2-pyridyl)methylthio-1,2,3,4-tetrazole

HRID 1758317Notes

Reaction equation

HRID 1758317 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.Cl[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].[I-]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 23393Picolyl chlorideHCID 30165Iodide IonHCID 178482017HCID 178482017, compound

Product 1

HCID 131384391-Methyl-5-(2-pyridyl)methylthio-1,2,3,4-tetrazoleYield 23.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (2.4 g) and 2-chloromethylpyridine (2.6 g) are dissolved in acetone (50 ml). To the mixture are added potassium carbonate (2.8 g) and patassium iodide (0.1 g), and the mixture is refluxed for 4 hours. After acetone is distilled off, water is added to the residue and extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium chloride and dried over sodium sulfate. After chloform is distilled off, the residue is purified by column chromatography (neutral alumina, made by Merck) and eluted with n-hexane to give 1-methyl-5-(2-pyridyl)methylthio-1,2,3,4-tetrazole (1.0 g) as colorless prisms (ethanol), m.p. 78°-81° C.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. distillationAfter acetone is distilled off
  3. additionwater is added to the residue
  4. extractionextracted with chloroform
  5. washThe chloroform solution is washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationAfter chloform is distilled off
  8. customthe residue is purified by column chromatography (neutral alumina, made by Merck)
  9. washeluted with n-hexane

Sources & evidence

ORD record
ord-b8020bc0ea274eacb72ea0fddaf293cf
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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