1-Chloro-3-nitro-2-(propan-2-ylsulfanyl)benzene → 3-Chloro-2-(isopropylthio)aniline

Participants

Reaction Conditions

Reaction Steps

40 g of 2-chloro-6-nitrophenyl-isopropylsulfane, 160 g of methanol and 2.4 g of Raney nickel 37-1 (methanol-moist) were initially introduced into a 0.7 l steel autoclave. After rinsing with nitrogen, 70 bar of hydrogen were forced in and the contents of the autoclave were heated to 100° C., while stirring. The hydrogen pressure was increased to 80 bar. After 50 minutes, the uptake of hydrogen had ended. The mixture was kept under the reaction conditions for a further 30 minutes. After cooling, letting down the hydrogen and removing the catalyst, the solvent was distilled off. Crude 2-amino-6-chlorophenyl-isopropylsulfane was already obtained as a 99% pure product (GC) which contained only 0.2% of 2-aminophenyl-isopropylsulfane (formed by dechlorination) and only 0.3% of m-chloroaniline (formed by desulfurization). The yield was 34.5 g.

Provenance & Evidence