Potassium Iodide → 1-Methyl-5-[3-(3-hydroxy-2-pyridyl)thiopropyl]thio-1,2,3,4-tetrazole

HRID 1758325Notes

Reaction equation

HRID 1758325 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10]Cl)=[N:5][N:4]=[N:3]1.[OH:12][C:13]1[C:14]([SH:19])=[N:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][S:19][C:14]2[C:13]([OH:12])=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 128033761-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazoleHCID 178516238HCID 178516238, compound

Product 1

HCID 130619411-Methyl-5-[3-(3-hydroxy-2-pyridyl)thiopropyl]thio-1,2,3,4-tetrazoleYield 42.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole (1.9 g) and 3-hydroxy-2-mercaptopyridine (1.3 g) are dissolved in acetone (50 ml). To the mixture are added potassium carbonate (1.4 g) and potassium iodide (0.1 g), and the mixture is refluxed for 5 hours. After acetone is distilled off, water is added to the residue, and the mixture is extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium chloride and dried over magnesium sulfate. After chloroform is distilled off, the residue is purified by column chromatography (Kieselgel 60), followed by eluting with chloroform-methanol and recrystallizing from ethyl acetate-n-hexane to give 1-methyl-5-[3-(3-hydroxy-2-pyridyl)thiopropyl]thio-1,2,3,4-tetrazole (1.2 g) as pale yellow granules, m.p. 87.5°-88.5° C.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. distillationAfter acetone is distilled off
  3. additionwater is added to the residue
  4. extractionthe mixture is extracted with chloroform
  5. washThe chloroform solution is washed with saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationAfter chloroform is distilled off
  8. customthe residue is purified by column chromatography (Kieselgel 60)
  9. washby eluting with chloroform-methanol
  10. customrecrystallizing from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-eb0192b257b94d2e9aafeb118d3ce033
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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