Chlorosuccinimide → 2,3,4-Trichloro-6-nitrobenzenamine
Reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Cl:13]N1C(=O)CCC1=O>CN(C)C=O>[Cl:13][C:7]1[C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
4,5-Dichloro-2-nitroaniline (15.2 g, 73.2 mmol), N-chlorosuccinimide (12.2 g, 91.6 mmol) and N,N-dimethylformamide (150 mL) were combined and the resulting orange solution was heated to 100° C. for 1 h. The solution was allowed to cool to room temperature and was poured into a flask containing ice water (1.2 L). The yellow solid was collected and was dissolved in dichloromethane (1.5 L), resulting in two-phases. The organic layer was collected and was dried over magnesium sulfate, filtered and the solvents were removed under reduced pressure by rotary evaporation to leave 17.6 g (98%) of a yellow solid. MS (Cl): m/z 239.