Potassium Carbonate → HCID 13061982, compound

HRID 1758299Notes

Reaction equation

HRID 1758299 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6].[CH3:14][N:15]1[C:19]([SH:20])=[N:18][N:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([CH2:4][CH2:3][CH2:2][S:20][C:19]1[N:15]([CH3:14])[N:16]=[N:17][N:18]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20509852HCID 20509852, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 13061982HCID 13061982, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Pyridyl 3-chloropropyl sulfone (2.2 g) and 1-methyl-5-mercapto-1,2,3,4-tetrazole (1.2 g) are dissolved in acetone (50 ml). Potassium carbonate (1.4 g) is added to the solution and the mixture is refluxed for 5 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 3-(1-methyl-1,2,3,4-tetrazol-5-yl)thiopropyl 2-pyridyl sulfone (1 g) as colorless prisms, m.p. 98.5°-101° C.

Workup

  1. temperaturethe mixture is refluxed for 5 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-9baef6bc153a45dfa94142ed82f78de1
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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