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

HRID 1758310Notes

Reaction equation

HRID 1758310 reaction equation
Cl.[CH3:2][N:3]1[C:7]([S:8][C:9](=N)N)=[N:6][N:5]=[N:4]1.[OH-].[Na+].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([CH2:22][CH2:23]CCl)=[O:21]>C(O)C>[CH3:2][N:3]1[C:7]([S:8][CH2:9][CH2:23][CH2:22][C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)=[O:21])=[N:6][N:5]=[N:4]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 124710063-Chloropropyl 2-pyridyl ketoneHCID 20509850S-(1-Methyl-1,2,3,4-tetrazole-5-yl)isothiourea hydrochloride

Product 1

HCID 130916431-Methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazoleYield 19.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

S-(1-Methyl-1,2,3,4-tetrazole-5-yl)isothiourea hydrochloride (1.9 g) is dissolved in ethanol (50 ml). To the solution are added 10% aqueous sodium hydroxide (5 ml) and 3-chloropropyl 2-pyridyl ketone (1.8 g) and the mixture is refluxed for 2 hours. Ethanol is distilled off and water is added to the residue. The mixture is extracted with chloroform. The chloroform solution is washed with water and saturated aqueous sodium chloride and dried over magnesium sulfate. Chloroform is distilled off and the residue is purified by column chromatography (Wakogel C-200, eluant: chloroform) 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 refluxed for 2 hours
  2. distillationEthanol is distilled off
  3. additionwater is added to the residue
  4. extractionThe mixture is extracted with chloroform
  5. washThe chloroform solution is washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationChloroform is distilled off
  8. customthe residue is purified by column chromatography (Wakogel C-200, eluant: chloroform)
  9. customthe product is recrystallized from hexane-ether

Sources & evidence

ORD record
ord-4d76038b22ca4d95bf7c1f20e2a37ceb
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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