Ethyl 2-bromopropionate → HCID 15016307, compound

HRID 2106625Notes

Reaction equation

HRID 2106625 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([N:10]2[CH:14]=[N:13][C:12]([OH:15])=[N:11]2)[CH:6]=[C:7]([Cl:9])[CH:8]=1.Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C.CS(C)=O>[Cl:9][C:7]1[CH:6]=[C:5]([N:10]2[CH:14]=[N:13][C:12]([O:15][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:23])=[N:11]2)[CH:4]=[C:3]([Cl:2])[CH:8]=1

Participants

6

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178518015HCID 178518015, compound

Product 1

HCID 15016307HCID 15016307, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

A 1.8 g portion of sodium was dissolved in 75 ml of absolute ethanol, and the solution was added slowly with stirring to a solution of 18.5 g of 1-(3,5-dichlorophenyl)-3-hydroxy-1,2,4-1H-triazole in 200 ml of dimethylsulfoxide. The solution was stirred at 60° for 1 hour, 14.5 g of ethyl 2-bromopropionate was added, and the mixture was heated for 2 hours at 100°-110°. It was then poured over ice water, and the solid was collected, dried and recrystallized from ether to obtain 10 g of the desired product. The mother liquor was chromatographed to obtain 1.3 g of additional product.

Workup

  1. additionthe solution was added slowly
  2. temperaturethe mixture was heated for 2 hours at 100°-110°
  3. customthe solid was collected
  4. customdried
  5. customrecrystallized from ether

Sources & evidence

ORD record
ord-5050af3077a349a3a705dfecfa67612e
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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