反应详情

2-Aminomethyl-4,5-bis(4-methoxyphenyl)thiazole hydrochloride (1.00 g) was added to a mixture of dichloromethane and saturated aqueous solution of sodium hydrogencarbonate, and was extracted with dichloromethane. The organic layer was washed with water, and brine, and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and resulting residue was dissolved in dimethylformamide (25 ml). To the resulting mixture was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.64 g) and 3-pyridylacetic acid hydrochloride (0.52 g), and stirred at ambient temperature for 2 hours and stirred at 60° C. for 5 hours. After allowing to cool to ambient temperature, the mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate, water, and brine, and dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The residue was subjected to column chromatography on silica gel (50 g) and eluted with a mixture of methanol and chloroform. The fractions containing the object compound were combined and evaporated in vacuo, and the resulting residue was dissolved in ethanol, and added an ethanol solution of hydrogen chloride. The mixture was evaporated in vacuo, and the resulting precipitate was collected by filtration and washed with diethyl ether, to give 4,5-bis(4-methoxyphenyl)-2-(3-pyridylacetylaminomethyl)thiazole hydrochloride (0.52 g).

1. extractionwas extracted with dichloromethane
2. washThe organic layer was washed with water, and brine
3. dry with materialdried over magnesium sulfate
4. filtrationAfter filtration
5. customthe filtrate was evaporated in vacuo
6. customresulting residue
7. stirringstirred at 60° C. for 5 hours
8. temperatureto cool to ambient temperature
9. extractionextracted with ethyl acetate
10. washThe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate, water, and brine
11. dry with materialdried over magnesium sulfate
12. additiontreated with activated charcoal
13. filtrationAfter filtration
14. customthe filtrate was evaporated in vacuo
15. washeluted with a mixture of methanol and chloroform
16. additionThe fractions containing the object compound
17. customevaporated in vacuo
18. dissolutionthe resulting residue was dissolved in ethanol
19. additionadded an ethanol solution of hydrogen chloride
20. customThe mixture was evaporated in vacuo
21. filtrationthe resulting precipitate was collected by filtration
22. washwashed with diethyl ether