Water → 6-Octylbenzo[d]thiazol-2-amine

Participants

Reaction Steps

In a 2 liters-reaction vessel, 50.0 g (0.24M) of p-octylaniline, 47.3 g (0.49M) of potassium thiocyanate and 350 ml of acetic acid were placed and cooled below 10° C. Under intersive stirring, a solution of 39.0 g of bromine in 120 ml of acetic acid was added dropwise to the above mixture in 75 minutes below 10° C., followed by reaction for 2 hours below 10° C. After the reaction, 500 ml of water was added to the reaction mixture and heated to dissolve the precipitate, followed by filtration under heating. Ammonia water was added to the filtrate so as to provide a basic solution, followed by cooling on an iced bath to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water and drying to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate) to obtain 41.2 g of 2-amino-6-octylbenzothiazole (Yield: 68%).

Provenance & Evidence