Thiophenol → HCID 178420567, compound

HRID 1758330Notes

Reaction equation

HRID 1758330 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][S:12][C:13]1[NH:17][N:16]=[N:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:2]1([S:1][CH2:9][CH2:10][CH2:11][S:12][C:13]2[NH:17][N:16]=[N:15][N:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 178419555HCID 178419555, compound

Product 1

HCID 178420567HCID 178420567, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Mercaptobenzene (1.3 g) and 5-(3-bromopropyl)thio-1,2,3,4-tetrazole (1.8 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 layer is washed with 5% aqueous sodium hydroxide and saturated aqueous sodium chloride and dried over magnesium sulfate. After chloroform is distilled off, the residue is purified by column chromatography (Wakogel C-200, eluting agent, chloroform) to give 5-(3-phenylthiopropyl)thio-1,2,3,4-tetrazole (1.5 g) as colorless liquid.

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 layer is washed with 5% aqueous sodium hydroxide and 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 (Wakogel C-200, eluting agent, chloroform)

Sources & evidence

ORD record
ord-a50ac9fe784e4e85a9774dba52546c22
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…