Sodium Chloride → HCID 14999093, compound

HRID 1030557Notes

Reaction equation

HRID 1030557 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) 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 in limited amounts 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) (compound No. 9) and the trans-isomer (2.1 g) (compound No. 10) of the title compound (55% yield). Compound No. 9: cis-isomer NMR (CDCl3, δ) [ppm]; 1.24 (3 H, t, J=7.2 Hz), 1.67 (3 H, d, J=7.1 Hz), 5.81 (1 H, s). IR (CHCl3) [cm-1 ]; 2950, 1740, 1683, 1587, 1575, 1441, 1370, 1014. Compound No. 10: trans-isomer NMR (CDCl3, δ) [ppm]; 1.25 (3 H, t, J=7.2 Hz), 1.68 (3 H, d, J=7.1 Hz), 5.83 (1 H, d, J=1.7 Hz). IR (CHCl3) [cm-1 ]; 2950, 1739, 1685, 1585, 1572, 1370, 1345, 1012.

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) (compound No. 9)

Sources & evidence

ORD record
ord-555170571f334f72b27f4b66f9735225
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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