HCID 19858390, compound → HCID 20195686, compound

Participants

Reaction Conditions

Reaction Steps

The dark phenolate/DMSO solution was allowed to cool to about 35° C. in an oil bath. N-4-benzocyclobutenyl 4-nitrophthalimide (1.00g, 3.40 mmol) was added next. The resultant reaction mixture was stirred under N2 at 30°-35° C. for another 21/2 hours. Then, the reaction mixture was poured into a separatory funnel containing about 300 ml of H2O and extracted with ethyl acetate (100 ml, 3×50 ml). The organic extract was then washed with saturated NaCl solution (2×150 ml) and dried over MgSO4. The volume of the dried extract was concentrated on a rotary evaporator to about 10 ml and passed through a chromatographic column containing about 100 g of silica gel saturated with petroleum ether. Elution was carried out with 100 ml petroleum ether, followed by 1:2 CH2Cl2 / petroleum ether. 4 bands were developed in the column. The desired product which was contained in the first band, was isolated as light yellow microcrystals. Yield: 0.45 g (30%). Calc. for C30H19NO3 : 81.62% C; 4.34% H; 3.17% N. Found: 81.05% C; 4.31% H; 3.09% N. Mass Spectroscopy: 441 (M+, 100%). Proton NMR (CDCl3): 3.20 (singlet, alicyclic protons); 7.00-7.93, (complex, aromatic protons). IR(KBr): 2700 m (alicyclic C--H stretches); 1706 m, 1778 vs (symmetric and asymmetric stretches of imide group): 1238 ms (Ar--O--Ar stretch).

Provenance & Evidence