Sodium Chloride → HCID 14999101, compound

HRID 1493252Notes

Reaction equation

HRID 1493252 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 portionwise to the mixture under ice-cooling. Then, the mixture was kept cooling for 1 hour. The resulting 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).

Workup

  1. additionwas added portionwise to the mixture under ice-
  2. temperaturecooling
  3. temperatureThen, the mixture was kept cooling for 1 hour
  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-fa6ffdd2050846a5be22eb1a9a2791c2
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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