Potassium Carbonate → HCID 13061942, compound

HRID 1758297Notes

Reaction equation

HRID 1758297 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.ClC[CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20509836HCID 20509836, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 13061942HCID 13061942, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (1.2 g) is dissolved in acetone (50 ml). To the solution are added 2-(3-chloropropyl)thiopyridine (2.0 g) and potassium carbonate (1.5 g) and the mixture is refluxed for 4 hours. Acetone is distilled off and water is added to the residue. The mixture is extracted with chloroform. The chloroform solution is washed with 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 and the product is recrystallized from ethanol to obtain 1-methyl-5-[2-(2-pyridyl)thioethyl]thio-1,2,3,4-tetrazole (1.5 g) as colorless prisms, m.p. 77°-79.5° C.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. distillationAcetone 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. distillationChloroform is distilled off
  8. customthe residue is purified by column chromatography (Kieselgel 60)
  9. washThe column is eluted with chloroform-methanol
  10. customthe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-fbf7dc12cd2346c9ae08e2eba8b90469
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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