4-Aminothiophenol → HCID 19980026, compound

Participants

Reaction Steps

Sodium metal (24 g, 1.05 mol) was added cautiously, in small portions, to 1 liter of stirred absolute ethanol under nitrogen. When the sodium has dissolved, 125 g (1.0 mol) of 4-aminothiophenol was added slowly. 6-Chlorohexanol (143 g, 1.05 mol) was added in small portions, and the resulting mixture was heated at reflux with stirring for one hour. The reaction mixture was cooled, filtered, and the ethanol was evaporated at reduced pressure. The residue was taken up in dichloromethane, and the solution was washed with water, with 5% NaHCO3 and again with water. The organic layer was dried (Na2SO4), concentrated, and the solid residue was recrystallized from ethanol. A pale yellow solid was obtained, mass 156 g.

Provenance & Evidence