反应详情

To a solution of 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.50 g, 1.7 mmol) in tetrahydrofuran (10 mL) was added 2-thiophenecarbonyl chloride (0.36 mL, 3.4 mmol), and triethylamine (0.52 mL, 3.7 mmol) was added to the obtained mixture. The reaction mixture was stirred at room temperature for 10 min. Saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was dissolved in conc. hydrochloric acid (5 mL) and the mixture was stirred at 40° C. for 14 hrs. The reaction mixture was neutralized with aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) and crystallized from isopropyl ether-hexane to give the title compound (0.56 g, yield 82%).

1. additionwas added to the obtained mixture
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with saturated brine
4. customdried
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in conc. hydrochloric acid (5 mL)
7. stirringthe mixture was stirred at 40° C. for 14 hrs
8. extractionextracted with ethyl acetate
9. customThe extract was dried
10. concentrationconcentrated
11. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1)
12. customcrystallized from isopropyl ether-hexane