Potassium Iodide → 1-methyl-5-[3-(N,N-diethylamino)propylthio]-1,2,3,4-tetrazole

HRID 1758316Notes

Reaction equation

HRID 1758316 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.[CH2:8]([N:10]([CH2:13][CH2:14][CH2:15]Cl)[CH2:11][CH3:12])[CH3:9].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:15][CH2:14][CH2:13][N:10]([CH2:11][CH3:12])[CH2:8][CH3:9])=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 669183-Chloropropyl(diethyl)amineHCID 178482017HCID 178482017, compound

Product 1

HCID 128033771-methyl-5-[3-(N,N-diethylamino)propylthio]-1,2,3,4-tetrazoleYield 23.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (2.4 g) and N,N-diethyl-3-chloropropylamine (3.0 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, water is added to the residue 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,N-diethylamino)propylthio]-1,2,3,4-tetrazole (1.09 g) as colorless liquid, nD25 =1.5040.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. distillationAfter acetone is distilled off
  3. additionwater is added to the residue
  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-ab52b8a5b4474fadaa3d8e39dc7ad8c4
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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