Ethyl bromoacetate → HCID 13853976, compound

HRID 34905Notes

Reaction equation

HRID 34905 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][NH:3]1.[H-].[Na+].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>O1CCCC1>[O:1]=[C:2]1[CH2:6][S:5][CH2:4][N:3]1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 6375914-Thiazolidinone

Product 1

HCID 13853976HCID 13853976, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-oxothiazolidine (50 g) in tetrahydrofuran (900 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil) (22.6 g) in tetrahydrofuran (850 ml) at room temperature and the mixture was allowed to warm up to reflux temperature. After the mixture was refluxed for an additional 30 minutes, ethyl bromoacetate (60 ml) was added dropwise under that condition. The mixture was refluxed further 1 hour and then cooled. Insoluble materials were removed by filtration. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography by eluting with chloroform to give ethyl 4-oxo-3-thiazolidinylacetate (78.5 g) as light brown powder.

Workup

  1. temperatureto warm up
  2. temperatureto reflux temperature
  3. temperatureAfter the mixture was refluxed for an additional 30 minutes
  4. temperatureThe mixture was refluxed further 1 hour
  5. temperaturecooled
  6. customInsoluble materials were removed by filtration
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography
  9. washby eluting with chloroform

Sources & evidence

ORD record
ord-f55b41624f3049e8a1e0f3dc130644a9
Source dataset
uspto-grants-1988_08
Patent number
US04764514

Reaction notes

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