Dimethyl Sulfoxide → Ethyl 2-({1-[3-(trifluoromethyl)phenyl]-1H-1,2,4-triazol-3-yl}oxy)propanoate

HRID 2106571Notes

Reaction equation

HRID 2106571 reaction equation
[Na].CS(C)=O.[OH:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:8]=1.Br[CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CO>[CH2:27]([O:26][C:24]([CH:23]([O:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[N:8]=1)[CH3:29])=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178517993HCID 178517993, compound

Product 1

HCID 184260Ethyl 2-({1-[3-(trifluoromethyl)phenyl]-1H-1,2,4-triazol-3-yl}oxy)propanoateYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1.7 g portion of sodium was dissolved in 30 ml of methanol, and the solution was added to 150 ml of dimethylsulfoxide. To it was added 17 g of 3-hydroxy-1-(3-trifluoromethylphenyl)-1,2,4-1H-triazole, and the solution was heated on the steam bath for 90 minutes. To it was then added 13.4 g of ethyl 2-bromopropionate, and heating was continued for 90 minutes more. The mixture was then cooled and poured over ice-water. The solid was collected, dried and recrystallized from ethanol to obtain 20.5 g of the desired product, m.p. 100°-102°.

Workup

  1. temperaturethe solution was heated on the steam bath for 90 minutes
  2. temperatureheating
  3. temperatureThe mixture was then cooled
  4. customThe solid was collected
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-51bd434a4856482c822ae67587a037dd
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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