反应 #452428

反应方程式

4-toluenesulfonyl chloride

N-ethyl-N'-3-(1-pyrrolidinyl)propylurea

triethylamine

→

desired product

收率 67.0%

1-(3-(1-pyrrolidinyl)propyl)-3-ethylcarbodiimide

收率 67.0%

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   温度to maintain
2. 2
   其他the reaction at 0-5° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   温度the reaction mixture was warmed to room temperature
5. 5
   温度heated
6. 6
   温度to reflux for 4 hours
7. 7
   温度After cooling to room temperature
8. 8
   洗涤the reaction mixture was washed with saturated aqueous potassium carbonate (3×150 mL)
9. 9
   萃取extracted with dichloromethane
10. 10
    浓缩concentrated under reduced pressure
11. 11
    其他the solution decanted off from the solid
12. 12
    浓缩concentrated under reduced pressure

实验过程

To a solution of 31.0 gm (0.156 mole) N-ethyl-N'-3-(1-pyrrolidinyl)propylurea in 500 mL dichloromethane were added 62.6 gm (0.62 mole) triethylamine and the solution was cooled to 0° C. To this solution were then added 59.17 gm (0.31 mole) 4-toluenesulfonyl chloride in 400 mL dichloromethane dropwise at such a rate as to maintain the reaction at 0-5° C. After the addition was complete, the reaction mixture was warmed to room temperature and then heated to reflux for 4 hours. After cooling to room temperature, the reaction mixture was washed with saturated aqueous potassium carbonate (3×150 mL). The aqueous phases were combined and extracted with dichloromethane. All organic phases were combined and concentrated under reduced pressure. The resultant orange slurry was suspended in 250 mL diethyl ether and the solution decanted off from the solid. The slurry/decantation process was repeated 3 more times. The ether solutions were combined and concentrated under reduced pressure to give 18.9 gm (67%) of the desired product as a crude orange oil. A portion of the oil was distilled under vacuum to give a colorless oil distilling at 78-82° C. (0.4 mm Hg).

来源