Reaction #2139939

Reaction equation

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

2-chloroethanesulfonyl chloride

sodium carbonate

triethylamine

→

pure product

Yield 72.9%

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

Yield 72.9%

Solvents

CH2Cl2

ethyl acetate

Conditions

Workup

1. 1
   Otherat 0° C
2. 2
   Otherthe resulting reaction mixture
3. 3
   WashThe organic phase is washed with
4. 4
   Dryingwater (100 ml), dried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue is further dried under vacuum

Procedure

A suspension of 5.38 g (30.0 mmol) of N-hydroxy-5-norbornene-2,3-dicarboximide and CH2Cl2 (120 ml) is successively treated with 2-chloroethanesulfonyl chloride (6.3 ml, 60.0 mmol) at room temperature and triethylamine (12.5 ml, 90.0 mmol) at 0° C. Stirring is continued for 1.5 h at room temperature and the resulting reaction mixture is treated with 10% aqueous sodium carbonate solution (100 ml) and ethyl acetate (200 ml). The organic phase is washed with. water (100 ml), dried over Na2SO4, and concentrated. The residue is further dried under vacuum, providing 5.89 g of pure product as light-yellow solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.53 (d, 1H), 1.76-1.81 (m, 1H), 3.12 (s, 2H), 3.48 (s, 2H), 6.17 (s, 2H), 6.29 (d, 1H), 6.53 (d, 1H), 6.78 (dd, 1H).

Source