反应详情

温度

80 °C

A solution of 15.0 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester in 250 ml. of hexamethylphosphoric acid triamide is treated under nitrogen at 5° C. with 0.055 mol of sodium hydride (2.5 g. of a 55% dispersion in mineral oil) and then stirred at the same temperature for 15 minutes. At 5°-10° C. a solution of 15 g. of N,N-diethylchloroacetamide in 40 ml. of ethanol is added thereto and the mixture stirred for 30 minutes at room temperature and subsequently heated for 4 hours at 80° C. The mixture is cooled and poured into 2.5 liters of ice-water. After the addition of 150 g. of sodium chloride, the separated product is removed by filtration under suction, washed with water and then dissolved in methylene chloride. The aqueous layer is separated, the organic phase dried over sodium sulfate, filtered and evaporated to dryness. The residue is triturated with 100 ml. of ether, the unreacted starting material crystallizes out. The latter is removed by filtration under vacuum and washed with ether. The ethereal filtrate is evaporated to dryness. The oily residue is cooled and triturated with ether, crystals being obtained. Recrystallization from ethanol yields 5-chloro-2-[(diethylcarbamoyl)methyl]-3-phenylisoindole-1-carboxylic acid ethyl ester; melting point 118°-120° C.

1. customAt 5°-10° C.
2. stirringthe mixture stirred for 30 minutes at room temperature
3. temperatureThe mixture is cooled
4. additionAfter the addition of 150 g
5. customof sodium chloride, the separated product is removed by filtration under suction
6. washwashed with water
7. dissolutiondissolved in methylene chloride
8. customThe aqueous layer is separated
9. dry with materialthe organic phase dried over sodium sulfate
10. filtrationfiltered
11. customevaporated to dryness
12. customThe residue is triturated with 100 ml
13. customcrystallizes out
14. customThe latter is removed by filtration under vacuum
15. washwashed with ether
16. customThe ethereal filtrate is evaporated to dryness
17. temperatureThe oily residue is cooled
18. customtriturated with ether, crystals
19. custombeing obtained
20. customRecrystallization from ethanol