2,6-Dimethylaniline → (2,6-Dimethylanilino)acetonitrile
Reaction equation
C1(S([O-])(=O)=O)C=CC=CC=1.[C:11](#[N:13])[CH3:12].[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17]>C(OCC)(=O)C>[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH:17][CH2:12][C:11]#[N:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 158.5 g (0.804 mol) of benzenesulphonate-acetonitrile in 200 ml of ethyl acetate is run dropwise into a solution of 193.6 g (1.608 mols) of 2,6-dimethyl-aniline in 400 ml of ethyl acetate. The mixture is heated under reflux for 3 hours, cooled and the excess aniline benzenesulphonate is filtered off. The filtrate is evaporated to dryness. The residue is taken up in ether. Insoluble material is again filtered off and discarded. The ether is evaporated to dryness. The residue is taken up in a mixture of petroleum ether/benzene (3:4 v/v). The crystals which form are filtered off.