反应 #2139941

反应方程式

HCl

N-hydroxy-5-norbornene-2,3-dicarboximide

pyridine

2-chloroethanesulfonyl chloride

→

product

收率 73.0%

N-(2-chloroethanesulfonyloxy)-5-norbornene-2,3-dicarboximide

收率 73.0%

溶剂

CH2Cl2

ethyl acetate

反应条件

后处理

1. 1
   其他The layers are separated
2. 2
   萃取the aqueous layer is extracted once with ethyl acetate (280 ml)
3. 3
   干燥The combined organic extracts are dried over Na2SO4
4. 4
   其他evaporated under reduced pressure
5. 5
   其他leaving a colorless oil which
6. 6
   其他further dried under vacuum

实验过程

A solution of 12.5 g (70.0 mmol) of N-hydroxy-5-norbornene-2,3-dicarboximide and pyridine (6.2 ml, 77.0 mmol) in CH2Cl2 (105 ml) is treated dropwise with 2-chloroethanesulfonyl chloride (7.36 ml, 70.0 mmol) at 0° C., according to the procedure of W. C. Groutas, M. A. Stanga, J. C. Castrisos, E. J. Schatz, M. J. Brubaker J. Pharm. Sci. 1990, 79, 886-88. After stirring overnight at room temperature, the reaction mixture is diluted with ethyl acetate (280 ml) and then treated with 5% aqueous HCl (130 ml). The layers are separated and the aqueous layer is extracted once with ethyl acetate (280 ml). The combined organic extracts are dried over Na2SO4 and evaporated under reduced pressure, leaving a colorless oil which solidifies when further dried under vacuum. 15.6 g (73%) of the product are obtained as a white solid.

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