Potassium Carbonate → Methyl 2-(1H-tetrazol-1-yl)propanoate

HRID 1761935Notes

Reaction equation

HRID 1761935 reaction equation
Br[CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[NH:8]1[CH:12]=[N:11][N:10]=[N:9]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:8]1([CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[CH:12]=[N:11][N:10]=[N:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 178418441HCID 178418441, compound

Product 1

HCID 20042588Methyl 2-(1H-tetrazol-1-yl)propanoateYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
18 °C

Procedure

A mixture of methyl 2-bromopropionate (66.8 g), 1H-tetrazole (28.02 g), anhydrous potassium carbonate (110 g) and acetone (1000 cm3) was stirred together at the ambient temperature (ca. 18° C.) for 1 hour and then at reflux temperature for four hours. After keeping the mixture for a further 16 hours at the ambient temperature the insoluble component was removed by filtration and the filtrate concentrated by evaporation of the solvent under reduced pressure. The residual oil (60 g) was subjected to distillation and the fraction having a boiling point range from 78°-93° C. at 0.35 to 2.5 mm Hg collected to yeild methyl 2-(1,2,3,4-2H-tetrazol-2-yl)propionate (A; 22.3 g). The undistillable residue was dissolved in dichloromethane and purified by elution through a short silica column. The collected eluate was concentrated by evaporation of the solvent under reduced pressure to yield methyl 2-(1,2,3,4-1H-tetrazol-1-yl)propionate (B; 35 g, 99% pure by gas/liquid chromatographic analysis).

Workup

  1. temperatureat reflux temperature for four hours
  2. customfor a further 16 hours
  3. customat the ambient temperature
  4. customwas removed by filtration
  5. concentrationthe filtrate concentrated by evaporation of the solvent under reduced pressure
  6. distillationThe residual oil (60 g) was subjected to distillation
  7. customfrom 78°-93° C.
  8. customcollected to yeild methyl 2-(1,2,3,4-2H-tetrazol-2-yl)propionate (A
  9. dissolutionThe undistillable residue was dissolved in dichloromethane
  10. custompurified by elution through a short silica column
  11. concentrationThe collected eluate was concentrated by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4ce52661b05d493fb294b8e530bb824e
Source dataset
uspto-grants-1989_05
Patent number
US04829074

Reaction notes

Loading…