1-Bromo-3-chloropropane → 1-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole

HRID 1758284Notes

Reaction equation

HRID 1758284 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.Br[CH2:9][CH2:10][CH2:11][Cl:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:9][CH2:10][CH2:11][Cl:12])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178482017HCID 178482017, compound

Product 1

HCID 128033761-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazoleYield 111.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (4.6 g) and 1-bromo-3-chloropropane (9.4 g) are dissolved in acetone (100 ml). Potassium carbonate (6.8 g) is added to the solution and the mixture is refluxed for 3 hours. Acetone is distilled off and water is added to the residue. The mixture is extracted with chloroform and 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 silica gel column chromatography (Wakogel C-200 made by Wako Jun Yaku Co., Ltd.). The column is eluted with benzene-ether (5:1, V/V) to obtain 1-methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole (8.5 g) as colorless liquid. nD14 =1.5396

Workup

  1. temperaturethe mixture is refluxed for 3 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 silica gel column chromatography (Wakogel C-200 made by Wako Jun Yaku Co., Ltd.)
  9. washThe column is eluted with benzene-ether (5:1, V/V)

Sources & evidence

ORD record
ord-8ba8f7e1689149778c7e0901cf2d4630
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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