反応 #3038

反応方程式

carbon disulfide

diethyl ether

ethanolamine

→

desired subtitled intermediate

N-(2-hydroxyethyl)rhodanine

溶媒

ethanol

反応条件

後処理

1. 1
   その他at ambient temperature
2. 2
   その他for 16 hours
3. 3
   その他the resulting top layer was decanted
4. 4
   洗浄the residual oil washed twice with 50 ml of diethyl ether
5. 5
   workup.ADDITIONTo the oil was added a solution of 71 g of chloroacetic acid in 150 ml of 5N sodium hydroxide at 0° C
6. 6
   その他The cooling bath was removed
7. 7
   workup.ADDITIONThe mixture was poured into 400 ml of 6N hydrochloric acid
8. 8
   温度the resulting mixture heated to 91° C. for 20 minutes
9. 9
   その他The heat was removed
10. 10
    workup.WAITto stand for 5 hours at ambient temperature
11. 11
    その他An oily organic layer was separated from the aqueous layer
12. 12
    抽出the aqueous layer extracted twice with 250 ml of ethyl acetate
13. 13
    洗浄washed twice with a saturated sodium chloride solution
14. 14
    その他dried
15. 15
    濃縮concentrated in vacuo

実験手順

Sixty milliliters of carbon disulfide were added to 200 ml of diethyl ether. The solution was chilled to -5° C. and slowly added to a solution of 138 ml of ethanolamine in 250 ml of ethanol. After holding the mixture at ambient temperature for 16 hours, the resulting top layer was decanted and the residual oil washed twice with 50 ml of diethyl ether. To the oil was added a solution of 71 g of chloroacetic acid in 150 ml of 5N sodium hydroxide at 0° C. The cooling bath was removed and the reaction was allowed to stand for 75 minutes. The mixture was poured into 400 ml of 6N hydrochloric acid and the resulting mixture heated to 91° C. for 20 minutes. The heat was removed, and the solution allowed to stand for 5 hours at ambient temperature. An oily organic layer was separated from the aqueous layer and the aqueous layer extracted twice with 250 ml of ethyl acetate. The organic layers were combined, washed twice with a saturated sodium chloride solution, dried and concentrated in vacuo to provide 113.4 g of the desired subtitled intermediate, which was used without further purification.

出典