(4-Aminophenoxy)benzene → N-(p-phenoxyphenyl)-2,3-dichloromaleimide
Reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1=[C:17]([Cl:23])[C:18]([O:20][C:21]1=O)=[O:19]>C(O)(=O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([N:12]2[C:21](=[O:20])[C:16]([Cl:15])=[C:17]([Cl:23])[C:18]2=[O:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 28 g of p-phenoxyaniline and 28 g of dichloromaleic anhydride in 200 ml of glacial acetic acid was heated at reflux for 3 hours. Upon subsequent cooling, N-phenoxyphenyl-2,3 -dichloromaleimide crystallized and was collected by filtration. The 46 g (92% of theory) of crude material was washed with petroleum ether and air-dried. An analytical sample was prepared by recrystallization from glacial acetic acid, producing golden flakes of N-(p-phenoxyphenyl)-2,3-dichloromaleimide melting at 180°-181° C.