Sodium hydride → Ethyl 2-{[1-(4-chlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}propanoate

HRID 2106579Notes

Reaction equation

HRID 2106579 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([OH:13])=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[N:11][C:10]([O:13][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:23])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionateHCID 178518003HCID 178518003, compound

Product 1

HCID 163820Ethyl 2-{[1-(4-chlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}propanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Six g of 1-(4-chlorophenyl)-3-hydroxy-1,2,4-1H-triazole was added to a suspension of 1.5 g of sodium hydride in 225 ml of dimethylsulfoxide. The mixture was heated on the steam bath for 90 minutes. Then 5.5 g of ethyl 2-bromopropionate was added and the mixture was heated for 90 minutes more. It was then cooled and poured over ice-water, and the solid was collected, dried and recrystallized from toluene to obtain 1.5 g of the desired product, m.p. 62°-64°.

Workup

  1. temperatureThe mixture was heated on the steam bath for 90 minutes
  2. temperaturethe mixture was heated for 90 minutes more
  3. temperatureIt was then cooled
  4. customthe solid was collected
  5. customdried
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-3c81752852e9487eb4db2b13c5311517
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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