Sodium Chloride → HCID 14999119, compound

Temperature

-78 °C

n-Butyllithium solution (5 ml, 8 mmol) in hexane was added dropwise to a solution of diisopropylamine (1.42 ml, 7.96 mmol) in dry tetrahydrofuran at -30° to -40° 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). This reaction mixture was kept at that temperature for 1 hour. Then, ethyl iodide (1.24 g, 7.96 mmol) was added, and this reaction mixture was slowly warmed up to room temperature and maintained there for 30 minutes. The resulting mixture, after addition of aqueous NaCl, was extracted with ethyl acetate. The extract was washed with aqueous NaCl, dried, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography, giving 5-ethyl-3-(2-dimethylaminoethyl)-2-(3-pyridyl)thiazolidin-4-one (1.84 g, 83% yield). NMR (CDCl, δ) [ppm]; 1.06 (3 H, t, J=7.3 Hz), 2.15 (6 H, s), 3.75-3.85 (1 H, m), 4.00-4.05 (1 H, m), 5.86 (1 H, d, J=2.0 Hz).

1. waitThis reaction mixture was kept at that temperature for 1 hour
2. temperaturethis reaction mixture was slowly warmed up to room temperature
3. temperaturemaintained there for 30 minutes
4. extractionwas extracted with ethyl acetate
5. washThe extract was washed with aqueous NaCl
6. customdried
7. concentrationconcentrated by evaporation under reduced pressure
8. customThe residue was purified by column chromatography

ORD record

ord-5cdb64f0f670429eaafbe65820f16126

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05106860