Chlorosuccinimide → 2-(2-Chloro-ethoxy)-4-chloro-6-nitro-phenylamine
Reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH2:14].[Cl:15]N1C(=O)CCC1=O>C(#N)C>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([Cl:15])[CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH2:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-(2-chloro-ethoxy)-6-nitro-phenylamine (30.0 g, 0.14 mol), N-chlorosuccinimide and acetonitrile (1.3 L) was refluxed for 4 hours. The mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (500 ml). The organic layer was washed with water (2×250 ml) and brine (250 ml), dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to give an orange solid residue. Crystallization from ethyl acetate-hexanes gave 33.5 g (95.3%) of product as an orange solid: mp 109-110° C.; MS (EI) 250/252/254 m/e (M+).