Sodium Chloride → HCID 14649073, compound

Temperature

-78 °C

A n-butyllithium solution (10 ml, 16 mmol) in hexane was added to dropwise to a solution of diisopropylamine (2.84 ml, 15.9 mmol) in dry tetrahydrofuran (6 ml) at -20° to -30° C. The mixture was kept between those temperatures for 1 hour and then cooled to -78° C. Thereto was added dropwise a solution of 3-(2-dimethylaminoethyl)-2-(3-pyridyl)thiazolidin-4-one (2 g, 7.96 mmol) in dry tetrahydrofuran (10 ml). The resulting mixture was kept at -78° C. for 1 hour. After addition of methyl iodide (2.26 g, 15.9 mmol), this reaction mixture was slowly warmed up to the room temperature and allowed to stand overnight. The resulting 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 purified by column chromatography, giving 5,5-dimethyl-3-(2-dimethylaminoethyl)-2-(3-pyridyl)thiazolidin-4-one (257 mg, 12% yield).

1. waitThe resulting mixture was kept at -78° C. for 1 hour
2. temperaturethis reaction mixture was slowly warmed up to the room temperature
3. waitto stand overnight
4. extractionwas extracted with ethyl acetate
5. washThe extract was washed with aqueous NaCl
6. customdried
7. customthe solvent was removed in vacuo
8. customThe residue was purified by column chromatography

ORD record

ord-69a64443265c4b4aa0e301a2fc69efb3

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05021435