Reaction #53162

Reaction equation

N-methylsulphonyl-4-nitroaniline

potassium tert.butoxide

bromoacetonitrile

→

N-cyanomethyl-N-methylsulphonyl-4-nitroaniline

Solvents

DMSO

Conditions

Workup

1. 1
   workup.ADDITIONare added dropwise
2. 2
   workup.ADDITIONis poured onto ice water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic phase is washed with water
5. 5
   OtherThe residue thus obtained
6. 6
   Otheris recrystallised from ethanol

Procedure

3.24 g (15 mmol) of N-methylsulphonyl-4-nitroaniline are dissolved in 25 ml of DMSO and a total of 2.0 g (18 mmol) of potassium tert.butoxide are added batchwise. After 1 hour stirring at ambient temperature 2.7 g (23 mmol) of bromoacetonitrile are added dropwise. After 3 hours stirring at ambient temperature the mixture is poured onto ice water and extracted with ethyl acetate. The organic phase is washed with water and the solvent is eliminated in vacuo. The residue thus obtained is recrystallised from ethanol.

Source