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

HRID 1758296Notes

Reaction equation

HRID 1758296 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.[C:8]1([S:14][CH2:15][CH2:16][CH2:17]Br)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:17][CH2:16][CH2:15][S:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70618473-Bromopropyl phenyl sulfideHCID 178482017HCID 178482017, compound

Product 1

HCID 128182731-Methyl-5-(3-phenylthiopropyl)thio-1,2,3,4-tetrazoleYield 65.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (1.2 g) is dissolved in acetone (50 ml). To the solution are added 3-bromopropyl phenyl sulfide (2.5 g) and potassium carbonate (1.5 g) and the mixture is refluxed for 4 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 benzenechloroform (3:2) to obtain 1-methyl-5-(3-phenylthiopropyl)thio-1,2,3,4-tetrazole (1.8 g) as colorless liquid, nD18 =1.6008.

Workup

  1. temperaturethe mixture is refluxed for 4 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 benzenechloroform (3:2)

Sources & evidence

ORD record
ord-159e5b2aba034b1ea2f20e9e78b73d5b
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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