Reaction #2139941

Reaction equation

HCl

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

pyridine

2-chloroethanesulfonyl chloride

→

product

Yield 73.0%

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

Yield 73.0%

Solvents

CH2Cl2

ethyl acetate

Conditions

Workup

1. 1
   OtherThe layers are separated
2. 2
   Extractionthe aqueous layer is extracted once with ethyl acetate (280 ml)
3. 3
   DryingThe combined organic extracts are dried over Na2SO4
4. 4
   Otherevaporated under reduced pressure
5. 5
   Otherleaving a colorless oil which
6. 6
   Otherfurther dried under vacuum

Procedure

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.

Source