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

HRID 1758312Notes

Reaction equation

HRID 1758312 reaction equation
[CH3:1][N:2]1[C:6](Cl)=[N:5][N:4]=[N:3]1.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([CH2:16][CH2:17][CH2:18][SH:19])=[O:15].[OH-].[Na+]>CO>[CH3:1][N:2]1[C:6]([S:19][CH2:18][CH2:17][CH2:16][C:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=2)=[O:15])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 205098305-chloro-1-methyl-1H-1,2,3,4-tetrazoleHCID 205098683-Mercaptopropyl 2-pyridyl ketone

Product 1

HCID 130916431-Methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazoleYield 7.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methyl-5-chloro-1,2,3,4-tetrazole (1.4 g) and 3-mercaptopropyl 2-pyridyl ketone (1.8 g) is dissolved in methanol (100 ml). Sodium hydroxide (0.6 g) is added to the solution and the mixture is refluxed for 3 hours. Methanol is distilled off and water is added to the residue. The mixture is extracted with chloroform. The chloroform solution is washed with dil. aqueous sodium hydroxide, water and saturated aqueous sodium chloride and dried over sodium 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 (0.2 g) as colorless needles, m.p. 73°-75° C.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. distillationMethanol is distilled off
  3. additionwater is added to the residue
  4. extractionThe mixture is extracted with chloroform
  5. washThe chloroform solution is washed with dil. aqueous sodium hydroxide, water and saturated aqueous sodium chloride
  6. dry with materialdried over sodium 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-2125c9750b2542728d00db4aad8ce0e9
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…