反应详情

75 ml of dimethylformamide was added to a mixture of 15.0 g of 2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide, 9.5 g of 3-amino-N-ethylbenzamide, 8.7 g of sodium iodide and 11.6 g of calcium carbonate, and the mixture was stirred for 4.5 hours at 55° to 60° C. After cooling, an insoluble material was removed by filtration and, the filtrate was concentrated in vacuo. The residue was extracted with 500 ml of chloroform, and the extract was washed successively with a 10% sodium sulfite aqueous solution and a saturated aqueous solution of sodium chloride. The washings were extracted with 500 ml of chloroform, and the extract was added to the chloroform solution. The combined chloroform solution was dried over sodium sulfate, and the solvent was distilled off. 120 ml of 10% hydrochloric acid was added to the residue, and the mixture was washed 6 times with 30 ml of dichloroethane. The aqueous solution was made alkaline by adding sodium carbonate to form an aggluten-like material. The material was extracted with 300 ml of dichloroethane, and the extract was washed with a saturated aqueous solution of sodium chloride. The washings were extracted with 200 ml of dichloroethane. The extract was added to the above dichloroethane solution, and the mixture was dried over sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography on 390 g of silica gel using a mixture of ethyl acetate and ethanol (10:1 by volume) for elution to obtain a fraction containing a product. The solvent of the fraction was distilled off and the residue was recrystallized from a mixture of methanol and diethyl ether to give 10.0 g of 3-((2-((2-(3,4-dimethoxyphenyl)ethyl)amino)-2-oxoethyl)amino)-N-ethylbenzamide as colorless needles with m.p. 99° to 101° C.

1. temperatureAfter cooling
2. customan insoluble material was removed by filtration
3. concentrationthe filtrate was concentrated in vacuo
4. extractionThe residue was extracted with 500 ml of chloroform
5. washthe extract was washed successively with a 10% sodium sulfite aqueous solution
6. extractionThe washings were extracted with 500 ml of chloroform
7. additionthe extract was added to the chloroform solution
8. dry with materialThe combined chloroform solution was dried over sodium sulfate
9. distillationthe solvent was distilled off
10. addition120 ml of 10% hydrochloric acid was added to the residue
11. washthe mixture was washed 6 times with 30 ml of dichloroethane
12. additionby adding sodium carbonate
13. customto form an aggluten-like material
14. extractionThe material was extracted with 300 ml of dichloroethane
15. washthe extract was washed with a saturated aqueous solution of sodium chloride
16. extractionThe washings were extracted with 200 ml of dichloroethane
17. additionThe extract was added to the above dichloroethane solution
18. dry with materialthe mixture was dried over sodium sulfate
19. distillationThe solvent was distilled off
20. customthe residue was purified by column chromatography on 390 g of silica gel using
21. additiona mixture of ethyl acetate and ethanol (10:1 by volume)
22. washfor elution
23. customto obtain a fraction
24. additioncontaining a product
25. distillationThe solvent of the fraction was distilled off
26. customthe residue was recrystallized from a mixture of methanol and diethyl ether