Thiophenol → 1-Methyl-5-(3-phenylthiopropyl)thio-1,2,3,4-tetrazole

HRID 1758324Notes

Reaction equation

HRID 1758324 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10]Cl)=[N:5][N:4]=[N:3]1.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][N:4]=[N:3]1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 128033761-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole

Product 1

HCID 128182731-Methyl-5-(3-phenylthiopropyl)thio-1,2,3,4-tetrazoleYield 95.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

1-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole (1.9 g) and thiophenol (1.1 g) are dissolved in acetone (50 ml). To the mixture are added potassium carbonate (1.5 g) and potassium iodide (0.1 g), and the mixture is refluxed for 3 hours. After acetone is distilled off, water is added to the residue, and the mixture is extracted with ether. The ether solution is washed with diluted aqueous sodium hydroxide and saturated aqueous sodium chloride and dried over sodium sulfate. After ether is distilled off, the residue is purified by silica gel column chromatography (Kieselgel 60), followed by eluting with benzene-chloroform (3:2) to give 1-methyl-5-(3-phenylthiopropyl)thio-1,2,3,4-tetrazole (2.5 g) as colorless liquid, nD18 =1.6008.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. distillationAfter acetone is distilled off
  3. additionwater is added to the residue
  4. extractionthe mixture is extracted with ether
  5. washThe ether solution is washed with diluted aqueous sodium hydroxide and saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationAfter ether is distilled off
  8. customthe residue is purified by silica gel column chromatography (Kieselgel 60)
  9. washby eluting with benzene-chloroform (3:2)

Sources & evidence

ORD record
ord-64e13d223ac54e87b14e07808855cda1
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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