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

HRID 1758305Notes

Reaction equation

HRID 1758305 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([CH2:22][CH2:23][CH2:24]Cl)=[O:21]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:24][CH2:23][CH2:22][C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)=[O:21])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124710063-Chloropropyl 2-pyridyl ketoneHCID 178482017HCID 178482017, compound

Product 1

HCID 130916431-Methyl-5-[3-(2-pyridylcarbonyl)propyl]thio-1,2,3,4-tetrazoleYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (1.2 g), potassium carbonate (2.1 g) and 3-chloropropyl 2-pyridyl ketone (2.8 g) are added to acetone (50 ml) and the mixture is refluxed with stirring for 2 hours. The reaction mixture is concentrated to dryness under reduced pressure and the residue is dissolved in chloroform. Insolubles are filtered off and the filtrated is concentrate under reduced pressure. The residue is purified by silica gel column chromatography (Kieselgel 60, eluant: 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 (yield 50%) as colorless needles, m.p. 73°-75° C.

Workup

  1. temperaturethe mixture is refluxed
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. dissolutionthe residue is dissolved in chloroform
  4. filtrationInsolubles are filtered off
  5. concentrationthe filtrated is concentrate under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (Kieselgel 60, eluant: benzene-ether (10:1))
  7. customthe product is recrystallized from hexane-ether

Sources & evidence

ORD record
ord-2930339a71a54f5daff8065816d09d7f
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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