Potassium Iodide → HCID 12803384, compound

HRID 1758315Notes

Reaction equation

HRID 1758315 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.[CH2:8]([N:10]([CH2:15][CH2:16][CH2:17]Cl)[C:11](=[O:14])[CH2:12][CH3:13])[CH3:9].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:17][CH2:16][CH2:15][N:10]([CH2:8][CH3:9])[C:11](=[O:14])[CH2:12][CH3:13])=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 15580597HCID 15580597, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 12803384HCID 12803384, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (2.4 g) and N-ethyl-N-propionyl-3-chloropropylamine (3.6 g) are dissolved in acetone (50 ml). To the mixture are added potassium carbonate (2.8 g) and potassium iodide (0.1 g), and the mixture is refluxed for 4 hours. After acetone is distilled off, the residue is added to water and extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium chloride and dried over sodium sulfate. After chloroform 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-[3-(N-ethyl-N-propionylamino)propylthio]-1,2,3,4-tetrazole (1.2 g) as pale yellow liquid, nD21.5 =1.5220.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. distillationAfter acetone is distilled off
  3. additionthe residue is added to water
  4. extractionextracted with chloroform
  5. washThe chloroform solution is washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationAfter chloroform 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-657f3074524b4380a1bb752fa3face0c
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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