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

HRID 2106573Notes

Reaction equation

HRID 2106573 reaction equation
[Na].CS(C)=O.[Cl:6][C:7]1[CH:8]=[C:9]([N:13]2[CH:17]=[N:16][C:15]([OH:18])=[N:14]2)[CH:10]=[CH:11][CH:12]=1.Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CO>[Cl:6][C:7]1[CH:8]=[C:9]([N:13]2[CH:17]=[N:16][C:15]([O:18][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:26])=[N:14]2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178517995HCID 178517995, compound

Product 1

HCID 184261Ethyl 2-{[1-(3-chlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}propanoateYield 29.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2.2 g portion of sodium was dissolved in 75 ml of methanol and the solution was added to 100 ml of dimethylsulfoxide. To that was added 19.2 g of 1-(3-chlorophenyl)-3-hydroxy-1,2,4-1H-triazole, and the mixture was stirred on the steam bath for 4 hours. To it was then added 17.7 g of ethyl 2-bromopropionate, and heating was continued for 2 hours more. The mixture was then cooled and poured over ice-water, and the solid was collected, dried and recrystallized from ethanol and then from toluene to obtain 8.5 g of the desired product, m.p. 70°-72°.

Workup

  1. temperatureheating
  2. waitwas continued for 2 hours
  3. temperatureThe mixture was then cooled
  4. customthe solid was collected
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f6cc6917852f473ea8149fc1155f8331
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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