HCID 12692632, Verbindung → 4-[(4-methoxyphenyl)sulfanyl]aniline
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:7][CH:8]=1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 13.06 g of 4-(4-methoxy-phenylsulfanyl)-nitrobenzene from step 1 in 100 mL of ethanol was added 33.85 g of SnCl2−2H2O. The resulting mixture was stirred for 30 minutes at room temperature, then heated to reflux for 2 hours. The mixture was then cooled to room temperature, concentrated in vacuo, and treated with 20% aqueous NaOH. The solution was extracted three times with ethyl acetate, and the combined extracts were washed with water followed by brine, dried (MgSO4), after which the ethyl acetate was removed in vacuo. The resulting solid was chromatographed on SiO2 (70%/30% dichloromethane/hexanes) to afford 7.87 g (68%) of 4-(4-methoxy-phenylsulfanyl)-phenylamine. Mp: 91–92° C. MS M+H: 232.