Dichloromethane → 2-Chloro-5-(phenylsulphonyl)aniline
Reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[Cl:19])([O-])=O.ClCCl>C(O)C>[Cl:19][C:5]1[C:4]([NH2:1])=[CH:9][C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:11])=[O:12])=[CH:7][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
2-Nitro-4-(phenylsulfonyl)chlorobenzene (9.8 g) and stannous chloride dihydrate (33.5 g) were suspended in absolute ethanol (200 mL) and heated to 75° C. for 40 minutes. The solution was evaporated and the resulting material was cooled to 0° C. Water (100 mL) was added, and the pH was adjusted to 8.0 with aqueous sodium hydroxide. The resulting solids were removed by filtration and the aqueous filtrate was extracted with ethyl acetate. The combined ethyl acetate solutions were evaporated to give a brown solid. Chromatography, with dichloromethane as the eluent yielded the aniline as an orange solid (7.3 g); mp: 105°-107° C.; 250 MHz NMR: 5.96 (s,2), 7.02 (dd,1 J=8, 2), 7.34 (d,1, J=2), 7.41 (d,1, J=8), 7.61 (m,3), 7.88 (d,2, J=7); MS: m/z=268(M+1).