Ethyl 2-bromopropionate → HCID 14268789, compound

HRID 2106570Notes

Reaction equation

HRID 2106570 reaction equation
[OH:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:3]=1.C[O-].[Na+].Br[CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CS(C)=O>[CH2:23]([O:22][C:20]([CH:19]([O:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:3]=1)[CH3:25])=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 10942334Sodium MethoxideHCID 178518002HCID 178518002, compound

Product 1

HCID 14268789HCID 14268789, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Thirteen g of 3-hydroxy-1-(2,4-dichlorophenyl)-1,2,4-1H-triazole was added to a solution of sodium methoxide (prepared from 1.3 g of sodium and excess methanol) in 200 ml of dimethylsulfoxide. The solution was heated on a steam bath for 2 hours, and then 10 g of ethyl 2-bromopropionate was added and heating was continued for 1.5 hours more. The mixture was then cooled, poured over ice-water, and extracted with 200 ml of diethyl ether. The ether extract was washed with 1N hydrochloric acid, with saturated aqueous sodium bicarbonate, and finally with saturated brine, and was dried with sodium sulfate and phase separation paper. The solvent was removed under vacuum to obtain 16 g of the desired product, an oil.

Workup

  1. temperatureThe solution was heated on a steam bath for 2 hours
  2. temperatureheating
  3. temperatureThe mixture was then cooled
  4. extractionextracted with 200 ml of diethyl ether
  5. extractionThe ether extract
  6. washwas washed with 1N hydrochloric acid, with saturated aqueous sodium bicarbonate
  7. dry with materialfinally with saturated brine, and was dried with sodium sulfate and phase separation paper
  8. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2026f11c9459420db50fe49776da3239
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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