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

HRID 1758314Notes

Reaction equation

HRID 1758314 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([CH2:9][CH2:10][CH2:11]Cl)=[O:8].NC(N)=[S:15].[CH3:17][N:18]1[C:22](Cl)=[N:21][N:20]=[N:19]1.[OH-].[Na+]>C(O)C>[CH3:17][N:18]1[C:22]([S:15][CH2:11][CH2:10][CH2:9][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:8])=[N:21][N:20]=[N:19]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 124710063-Chloropropyl 2-pyridyl ketoneHCID 205098305-chloro-1-methyl-1H-1,2,3,4-tetrazole

Product 1

HCID 130916431-Methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazoleYield 7.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloropropyl 2-pyridyl ketone (1.8 g) and thiourea (0.8 g) are dissolved in ethanol (50 ml), and the solution is refluxed with stirring for 2 hours. To the mixture are added 1-methyl-5-chloro-1,2,3,4-tetrazole (1.2 g) and 10% aqueous sodium hydroxide (5 ml), and the mixture is refluxed for 3 hours. After evaporating ethanol under reduced pressure, water is added to the residue. The mixture is extracted with chloroform, and the extract is washed with water and saturated aqueous sodium chloride and dried over magnesium sulfate. After chloroform is distilled off, the residue is purified by column chromatography (Wakogel C-200, eluting agent, chloroform), followed by recrystallized from hexane-ether to give 1-methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazole (0.2 g) as colorless crystals, m.p. 73°-75° C.

Workup

  1. temperaturethe solution is refluxed
  2. temperaturethe mixture is refluxed for 3 hours
  3. customAfter evaporating ethanol under reduced pressure, water
  4. additionis added to the residue
  5. extractionThe mixture is extracted with chloroform
  6. washthe extract is washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. distillationAfter chloroform is distilled off
  9. customthe residue is purified by column chromatography (Wakogel C-200, eluting agent, chloroform)
  10. customby recrystallized from hexane-ether

Sources & evidence

ORD record
ord-bbdd61b1c32c4694819b9f8505046d5f
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…