Aniline → HCID 21184374, compound

Participants

Reaction Steps

To a solution of 200 mg (0.8 mmol) of 2-chloro-4,9-dihydro-4,9-dioxo-naphtho[2,3-d]thiazole in 100 mL of ethanol, 730 μL (8 mmol) of aniline are added at 80° C. The reaction mixture is heated to reflux for 3.5 h; the red precipitate obtained is filtered after cooling, then purified on a cake (support: silica 6-35 μm; eluant: dichloromethane/heptane, 20/80 to 100/0, then dichloromethane/ethyl acetate, 99.5/0.5 to 0/100). The clean fractions are combined, then filtered through micropores; the solvent is evaporated at reduced pressure to produce 196 mg of 4,9-dihydro-4,9-dioxo-2-phenylamino-naphtho[2,3-d]thiazole in the form of red crystals.

Provenance & Evidence