Ethyl 2-bromopropionate → HCID 15016248, compound

HRID 2106623Notes

Reaction equation

HRID 2106623 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[N:12][C:11](=[S:14])[NH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Na].Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CS(C)=O.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[N:12][C:11]([S:14][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:23])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 23048436HCID 23048436, compound

Product 1

HCID 15016248HCID 15016248, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

An 11.5 g portion of 1-(3,4-dichlorophenyl)3-thiono-1,2,4-1H-triazole was dissolved in 100 ml of dry dimethylsulfoxide, and was added to 1.1 g of sodium dissolved in 50 ml of absolute ethanol. The mixture was warmed at 60°-80° for 1 hour, and then 8.5 g of ethyl 2-bromopropionate was added and the mixture was held at 100°-110° for 2 hours. It was then cooled and poured over ice-water, and the aqueous mixture was extracted with dichloromethane. The organic layer was washed with brine, and was dried over magnesium sulfate. The solvent was removed under vacuum, and the residue was purified by chromatography, eluting with 2:1 hexane:ethyl acetate. The product-containing fractions were combined and evaporated under vacuum to obtain 11 g of the desired product.

Workup

  1. temperatureThe mixture was warmed at 60°-80° for 1 hour
  2. temperatureIt was then cooled
  3. extractionthe aqueous mixture was extracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed under vacuum
  7. customthe residue was purified by chromatography
  8. washeluting with 2:1 hexane
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-35d055fbd39d4d47ab04b544bfcb8511
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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