4,4'-Bis(diethylamino) benzophenone

135-91-1

90-93-7

General procedure for the synthesis of tetraethyl mithridone from 4,4'-methylenebis(N,N-dimethylaniline): 4,4'-bis(dialkylamino)diphenylmethane (30g), cobalt complex (3) (0.9g), tetrachlorophenylhydrazine (0.9g), trioctylmethylammonium chloride (1g), and chlorobenzene (100 ml) were added into 250 ml four necked flask. At room temperature, 30% hydrogen peroxide (13.2 g) was slowly added dropwise and the reaction temperature was controlled between 20 and 25°C. The progress of the reaction was monitored by thin layer chromatography (TLC) until the ingredients were fully reacted. Upon completion of the reaction, the reaction mixture was cooled to 5 °C, washed by adding 30 ml of 20% sodium bisulfite solution, and left to stratify. The organic phase was concentrated by distillation under reduced pressure to give the crude product of tetraethyl mithridone (29 g). The crude product was recrystallized with n-heptane (29 g) to give a light yellow tetraethyl mesterolone solid (25.3 g), which was analyzed by high performance liquid chromatography (HPLC) and showed a purity of 99.1%.