Hydrochloric Acid → 1-Methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazole

HRID 1758301Notes

Reaction equation

HRID 1758301 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][C:11]2(OCC[O:18]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[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]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:18])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water2×HCID 205098851-Methyl-5-[4,4-ethylenedioxy-4-(2-pyridyl)butyl]thio-1,2,3,4-tetrazole

Product 1

HCID 130916431-Methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazoleYield 83.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Methyl-5-[4,4-ethylenedioxy-4-(2-pyridyl)butyl]thio-1,2,3,4-tetrazole (0.7 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 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) and the product is recrystallized from hexane-ether to obtain 1-methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazole, (0.5 g) as colorless needles, m.p. 73°-75° C.

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 and saturated aqueous sodium chloride
  4. dry with materialdried 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)
  8. customthe product is recrystallized from hexane-ether

Sources & evidence

ORD record
ord-8e86d79ee6ae4c39bc15c868857e7f2b
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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