Potassium Carbonate → HCID 13061980, compound

HRID 1758332Notes

Reaction equation

HRID 1758332 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:8]1[N:12]([CH3:13])[N:11]=[N:10][N:9]=1)=[O:7].[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>[CH3:14][N:15]1[C:19]([S:20][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:8]2[N:12]([CH3:13])[N:11]=[N:10][N:9]=2)=[O:7])=[N:18][N:17]=[N:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13061934HCID 13061934, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 13061980HCID 13061980, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-1,2,3,4-tetrazol-5-yl 4-bromobutyl sulfoxide (2.7 g) and 1-methyl-5-mercapto-1,2,3,4-tetrazole (1.4 g) are dissolved in acetone (50 ml), and thereto is added potassium carbonate (1.4 g), and the mixture is refluxed for 2 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), eluting with chloroform-methanol (100:1) to give 1-methyl-1,2,3,4-tetrazol-5-yl 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thiobutyl sulfoxide (1.5 g), as colorless liquid, nD19 =1.5660.

Workup

  1. temperaturethe mixture is refluxed for 2 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. washeluting with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-3629aba9d40e40e0902c79e05de5f0b5
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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