Bromoacetonitrile → n-Cyanomethyl-n-methylsulphonyl-4-nitroaniline

HRID 24884Notes

Reaction equation

HRID 24884 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3].CC(C)([O-])C.[K+].Br[CH2:22][C:23]#[N:24]>CS(C)=O>[C:23]([CH2:22][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[CH:7]=[CH:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1)#[N:24]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 4689022N-(4-nitrophenyl)methanesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22569517n-Cyanomethyl-n-methylsulphonyl-4-nitroaniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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.

Workup

  1. additionare added dropwise
  2. additionis poured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. customThe residue thus obtained
  6. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-dc456cbe6fbe4898aee71532eb090652
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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