Ethyl 2-bromopropionate → HCID 15016258, compound

HRID 2106581Notes

Reaction equation

HRID 2106581 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([OH:14])=[N:10]2)=[CH:5][CH:4]=1.Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C.CS(C)=O>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[N:12][C:11]([O:14][CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:22])=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178517954HCID 178517954, compound

Product 1

HCID 15016258HCID 15016258, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

A 3.9 g portion of sodium was dissolved in 50 ml of ethanol and was added to a solution of 41 g of 1-(4-bromophenyl)-3-hydroxy-1,2,4-1H-triazole in 150 ml of dimethylsulfoxide. The mixture was heated at 60° for 45 minutes, and then 30.9 g of ethyl 2-bromopropionate was added. The mixture was heated for 2 hours more, and was then cooled and poured over ice-water. The solid was collected and dried, and was recrystallized from toluene. The mother liquor was concentrated under vacuum, and the residue was recrystallized from ethanol. That product was combined with the first portion of product and recrystallized from ethanol to obtain 27.9 g of the desired product, m.p. 64°-66°.

Workup

  1. temperatureThe mixture was heated at 60° for 45 minutes
  2. temperatureThe mixture was heated for 2 hours more
  3. temperaturewas then cooled
  4. customThe solid was collected
  5. customdried
  6. customwas recrystallized from toluene
  7. concentrationThe mother liquor was concentrated under vacuum
  8. customthe residue was recrystallized from ethanol
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f7fe3712e7724fabbb6aafb536bc7ddc
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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