Sodium Chloride → HCID 14999101, compound

HRID 1030558Notes

Reaction equation

HRID 1030558 reaction equation
[CH3:1]I.[OH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]([CH3:12])[S:8][CH:7]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[H-].[Na+].[Na+].[Cl-]>CN(C)C=O>[CH3:1][O:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]([CH3:12])[S:8][CH:7]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14999089HCID 14999089, compound

Product 1

HCID 14999101HCID 14999101, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.72 g, 5.0 mmol) was added to a solution of 3-(2-hydroxyethyl)-5-methyl-2-(3-pyridyl)-thiazolidin-4-one (1 g, 4.2 mmol) in dry dimethylformamide (5 ml), and 40% sodium hydride (176 mg, 4.4 mmol) was added in limited amounts of the mixture under cooling with ice. Then, cooling with ice was continued for 1 hour. The product mixture was poured into aqueous NaCl, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated and subjected to medium-pressure chromatography (hexane-acetone), giving 3-(2-methoxyethyl)-5-methyl-2-(3-pyridyl)-thiazolidin-4-one (0.51 g, 48% yield). NMR (CDCl3) δ [ppm]; 1.62 (0.75 H, d, J=7.1 Hz), 1.66 (2.5 H, d, J=7.1 Hz), 3.28 (2.25 H, s), 3.3 (0.75 H, s), 5.85 (1 H, s) IR (CHCl3) [cm-1 ]; 2935, 1670, 1589, 1576, 1445, 1408, 1300, 1113.

Workup

  1. additionwas added in limited amounts of the mixture
  2. temperatureunder cooling with ice
  3. temperatureThen, cooling with ice
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0b31f91dd5174581bcd265e77f65e0c6
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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