Methyl iodide → HCID 14999101, compound

HRID 981558Notes

Reaction equation

HRID 981558 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+]>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

5

Reactant 3

HCID 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 solutoin 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 to the mixture under cooling with ice. Then, cooling with ice was continued for 1 hour. The product mixture was poured into aqueous NaC1, 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 in limited amounts to the mixture
  2. temperatureunder cooling with ice
  3. temperatureThen, cooling with ice
  4. additionThe product mixture was poured into aqueous NaC1
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b8046d70558340839d188d00a23b6c4c
Source dataset
uspto-grants-1991_02
Patent number
US04992455

Reaction notes

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