反应详情

21.5 ml (0.4 mol) of 100% sulfuric acid is dissolved, under cooling in 100 ml of methanol, the solution is heated under reflux for ½ hour, then cooled to room temperature and to it 33.1 g (0.1 mol) of [2-(2-thienyl)ethylamino](2-chlorophenyl)acetamide hydrochloride, prepared as described in Example 5., is added and the mixture is heated under reflux conditions for 10 hours. Methanol is then distilled off in vacuo and to the residue 150 ml of 1,2-dichloroethane and 150 ml of water are added, shaken well, and the two phases are separated. The aqueous layer is extracted with 2×30 ml of 1,2-dichloroethane, the combined organic layers are washed with 80 ml of 5% sodium hydroxide solution, then with 100 ml of water, dried over anhydrous sodium sulfate and evaporated in vacuo. Weight of the residue: 28.5 g. The oily product, which is the base of formula (VIII), is dissolved in 50 ml of isopropyl acetate, 7.3 ml (0.087 mol) of concentrated hydrochloric acid solution is added to it, and the mixture is stirred at room temperature for 1 hour. The precipitating product is filtered off, washed with 2×10 ml of isopropyl acetate and dried. Weight: 28.4 g (82%) mp.: 177-178° C. (lit. 175° C.).

1. temperaturethe solution is heated
2. temperatureunder reflux for ½ hour
3. customprepared
4. addition, is added
5. temperaturethe mixture is heated under reflux conditions for 10 hours
6. distillationMethanol is then distilled off in vacuo and to the residue 150 ml of 1,2-dichloroethane and 150 ml of water
7. additionare added
8. customthe two phases are separated
9. extractionThe aqueous layer is extracted with 2×30 ml of 1,2-dichloroethane
10. washthe combined organic layers are washed with 80 ml of 5% sodium hydroxide solution
11. dry with materialwith 100 ml of water, dried over anhydrous sodium sulfate
12. customevaporated in vacuo
13. dissolutionis dissolved in 50 ml of isopropyl acetate
14. stirringthe mixture is stirred at room temperature for 1 hour
15. filtrationThe precipitating product is filtered off
16. washwashed with 2×10 ml of isopropyl acetate
17. customdried
18. custom28.4 g (82%) mp.: 177-178° C. (lit. 175° C.)