Sodium Chloride → HCID 14999093, compound

HRID 1493251Notes

Reaction equation

HRID 1493251 reaction equation
[CH3:1][CH:2]1[S:6][CH:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:4][C:3]1=[O:13].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[H-].[Na+].[Na+].[Cl-]>CN(C)C=O>[CH2:19]([O:18][C:16]([CH2:15][N:4]1[C:3](=[O:13])[CH:2]([CH3:1])[S:6][CH:5]1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 14999088HCID 14999088, compound

Product 1

HCID 14999093HCID 14999093, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Methyl-2-(3-pyridyl)thiazolidin-4-one (10 g, 51.5 mmol) (cis and trans mixture) and ethyl bromoacetate (6.85 ml, 61.8 mmol) were dissolved in dry dimethylformamide (50 ml), and 60% sodium hydride (2.16 g, 54.1 mmol) was added portionwise to the solution at 0° to 10° C. This reaction mixture was kept between those temperatures for 1 hour. The mixture, after addition of aqueous NaCl, was extracted with ethyl acetate. The extract was washed with aqueous NaCl, dried, and the solvent was removed in vacuo. The residue was chromatographed on silica gel, giving the cis-isomer (5.8 g) and the trans-isomer (2.1 g) of the title compound (55% yield).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with aqueous NaCl
  3. customdried
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on silica gel
  6. customgiving the cis-isomer (5.8 g)

Sources & evidence

ORD record
ord-6d047fd032b34264a603ff5482b90039
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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