Chloroacetone → 2-Propanone, 1-((1-methyl-1H-tetrazol-5-yl)thio)-

HRID 1758302Notes

Reaction equation

HRID 1758302 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15]([CH2:17]Cl)=[O:16]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:14][C:15](=[O:16])[CH3:17])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 178482017HCID 178482017, compound

Product 1

HCID 30619772-Propanone, 1-((1-methyl-1H-tetrazol-5-yl)thio)-Yield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (0.01 mol), potassium carbonate (0.015 mol) and α-chloroacetone (0.015 mol) 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. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel column chromatography [Kieselgel 60, eluant: benzene-ether (10:1)] and the product is recrystallized from methanol-ether to obtain 1-methyl-5-acetylmethylthio-1,2,3,4-tetrazole (yield 48%) as colorless needles, m.p. 31° 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 filtrate is concentrated 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 methanol-ether

Sources & evidence

ORD record
ord-251cd1ba05c642a9817e905ef8c3e208
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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