Stannous Chloride → 4-(Methylthio)benzene-1,2-diamine

Participants

Reaction Steps

5-(Methylthio)-2-nitroaniline (12.9 g, 70.1 mmol) was dissolved In 475 mL of EtOH with stirring. Tin (II) Chloride (74.0 g, 392 mmol) was added and the reaction was refluxed for 20 h. The reaction was cooled to rt and concentrated in vacuo to a volume of 150 mL. The pH of the solution was adjusted to approximately 10 using concentrated aqueous 3N NaOH. EtOAc (1.5 L) was added and the reaction was filtered through Celite, washing with water and EtOAc. The aqueous layer was separated, then extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give 10.7 g (99%) of the crude 4-(methylthio)benzene-1,2-diamine as a dark oil. 1H NMR (400 MHz, DMSO-d6) δ 6.52 (m, 1H), 6.44 (m, 1H), 6.37 (m, 1H), 4.49 (br s, 4H), 2.29 (s, 3H).

Provenance & Evidence