Hydrochloric Acid → 1-Methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazole

HRID 1758300Notes

Reaction equation

HRID 1758300 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][C:11]2(OCC[O:14]2)[CH2:12][CH3:13])=[N:5][N:4]=[N:3]1.O.Cl>C(O)(=O)C>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH3:13])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water2×HCID 130916201-Methyl-5-(4,4-ethylenedioxyhexyl)thio-1,2,3,4-tetrazole

Product 1

HCID 130916231-Methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazoleYield 80.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Methyl-5-(4,4-ethylenedioxyhexyl)thio-1,2,3,4-tetrazole (0.6 g) is dissolved in acetic acid (5 ml). Water (2.5 ml) and conc. hydrochloric acid (0.5 ml) are added to the solution and the mixture is heated on a water bath for 1 hour. Water is added to the reaction mixture and the mixture is extracted with chloroform. The chloroform solution is washed with water, saturated aqueous sodium bicarbonate and then saturated aqueous sodium chloride and dried over magnesium sulfate. Chloroform is distilled off and the residue is purified by silica gel column chromatography (Kieselgel 60). The column is eluted with benzene-ether (10:1) to obtain 1-methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazole (0.4 g) as colorless liquid, nD25 =1.5042.

Workup

  1. temperaturethe mixture is heated on a water bath for 1 hour
  2. extractionthe mixture is extracted with chloroform
  3. washThe chloroform solution is washed with water, saturated aqueous sodium bicarbonate
  4. dry with materialsaturated aqueous sodium chloride and dried over magnesium sulfate
  5. distillationChloroform is distilled off
  6. customthe residue is purified by silica gel column chromatography (Kieselgel 60)
  7. washThe column is eluted with benzene-ether (10:1)

Sources & evidence

ORD record
ord-928dc000799e4656adacfa0e8a5404ba
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…