Dimethyl Sulfoxide → 3-(1-ethoxycarbonylethoxy)-5-methyl-1-phenyl-1,2,4-1H-triazole

HRID 2106575Notes

Reaction equation

HRID 2106575 reaction equation
[Na].CS(C)=O.[OH:6][C:7]1[N:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=1.Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CO>[CH2:24]([O:23][C:21]([CH:20]([O:6][C:7]1[N:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:8]=1)[CH3:26])=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178433514HCID 178433514, compound

Product 1

HCID 150162493-(1-ethoxycarbonylethoxy)-5-methyl-1-phenyl-1,2,4-1H-triazoleYield 51.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3.2 g portion of sodium was dissolved in 50 ml of methanol, and the solution was added to 100 ml of dimethylsulfoxide. To it was added 24.6 g of 3-hydroxy-5-methyl-1-phenyl-1,2,4-1H-triazole, and the solution was heated on the steam bath for 2 hours, adding 100 ml of additional dimethylsulfoxide. To the solution was then added 25.4 g of ethyl 2-bromopropionate, and heating was continued for 2 hours more. The reaction mixture was then cooled, poured over ice-water, and extracted with 300 ml of chloroform. The extract was washed with water and with saturated brine, and was dried with sodium sulfate and phase separation paper. The solvent was removed under vacuum, and the product was distilled at 1.2 mm of mercury and 192° to obtain 20 g of the desired product, an oil.

Workup

  1. temperaturethe solution was heated on the steam bath for 2 hours
  2. temperatureheating
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted with 300 ml of chloroform
  5. washThe extract was washed with water and with saturated brine
  6. dry with materialwas dried with sodium sulfate and phase separation paper
  7. customThe solvent was removed under vacuum
  8. distillationthe product was distilled at 1.2 mm of mercury and 192°

Sources & evidence

ORD record
ord-4605f400e55d475daf1516f72c8749b6
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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