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

Participants

Reaction Conditions

Reaction Steps

46.6 g of 2-chloro-6-nitrophenyl-isopropylsulfane, 160 ml of methanol and 5 g of Raney nickel 55 (water-moist, washed with methanol) were introduced into a steel autoclave. After flushing with nitrogen and hydrogen, the mixture was heated to 50° C., while stirring, and hydrogenation was carried out by forcing in hydrogen up to a maximum of 2 bar. After 2.5 hours, the uptake of hydrogen had ended. The mixture was then cooled to room temperature, the hydrogen was let down and the nickel catalyst was removed by filtration with suction and washed with methanol. After removal of the solvent, 39.9 g of 2-amino-6-chlorophenyl-isopropylsulfane were obtained in a purity of 97.8% (GC), which corresponds to 97% of theory. Only 0.2% of 2-aminophenylisopropylsulfane (formed by dehalogenation) was found as an impurity. Pure, colorless 2-amino-6-chlorophenyl-isopropylsulfane with a content of more than 99% was obtained by distillation at a boiling point of 144° C. at 11 mbar.

Provenance & Evidence