Reaction #46433

Reaction equation

11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

4-(trifluoromethyl)phenyl isothiocyanate

→

desired product

Yield 90.1%

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

Yield 90.1%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe solvent was then evaporated under reduced pressure

Procedure

200 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.60 mmole) were dissolved in 10 ml of acetonitrile. 244 mg (2 molar equivalents) of 4-(trifluoromethyl)phenyl isothiocyanate was added and the reaction mixture was maintained at room temperature for 16 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography (SiO2, CH2Cl2/MeOH 95/5). 290 mg of the desired product (formula shown hereinabove) were isolated as a red powder (yield=90%) which was characterized as follows:

Source