4-Methoxyphenyl isothiocyanate → 1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-methoxyphenyl]thiourea

Participants

Reaction Steps

300 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.90 mmole) are dissolved in 20 ml of acetonitrile. 250 μl (2 molar equivalents) of 4-methoxyphenyl isothiocyanate was added and the reaction mixture was maintained at room temperature for 16 hours. Two more equivalents of 4-methoxyphenyl isothiocyanate was added and the reaction mixture was stirred for 24 hours at room temperature. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography (SiO2, CH2Cl2/MeOH 95/5). 409 mg of UN the desired product (formula shown hereinabove) were isolated as a red powder (yield=91%) which was characterized as follows:

Provenance & Evidence