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

HRID 1758306Notes

Reaction equation

HRID 1758306 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]1[N:16]=[CH:17][S:18][C:19]=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:19]2[S:18][CH:17]=[N:16][C:15]=2[CH3:14])=[O:21])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20509861HCID 20509861, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 132192111-Methyl-5-[3-(4-methyl-5-thiazolylcarbonyl)propyl]thio-1,2,3,4-tetrazoleYield 88.8%

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 4-methyl-5-thiazolyl ketone (3.1 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 concentrated 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-(4-methyl-5-thiazolylcarbonyl)propyl]thio-1,2,3,4-tetrazole (2.6 g) as colorless needles, m.p. 64°-65° 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 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 hexane-ether

Sources & evidence

ORD record
ord-c5d7422ada2944a697427b07bbba9811
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…