Thionyl Chloride → 4-(Chloromethyl)-N-methyl-2-nitroaniline
Reaktionsgleichung
[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].S(Cl)([Cl:16])=O>>[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:16])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]Komponenten
3
Versuchsvorschrift
1.0 g (5.5 mmol) of 9 was dissolved in 25 ml thionylchloride at -78° C. cooled with dry ice/acetone bath. After it dissolved completely, the dry ice/acetone bath was removed and the reaction mixture allowed to warm up to room temperature and kept at room temperature for additional 1 hour. Thionylchloride was evaporated under vacuum at room temperature and the residue was washed with 5 ml cold diethylether and recrystallized from diethylether to yield 0.6 g (55%) of 10. Yellow, mp: 126°-128° C. 1H NMR: (DMSO-d6): δ 82.9 (s, 1H, NH), 8.15 (d, 1H, J=2.2 Hz, H-2), 7.60p, 1H, (dd, 1H, J=8.9, 2.2 Hz, H-6), 7.01 (d, 1H, J=9.0 Hz, H-5), 4.76 (s, 3H, CH2), 2.95 (s, 3H, CH3). Anal. Calcd for C8H9N2O2Cl: C, 47.89; H, 4.52; Cl, 17.67; N, 14.00; O, 15.95. found: C, 47.78; H, 4.49; Cl, 17.78; N, 13.82; O, 16.13.