Imidazole → HCID 19033237, compound

Participants

Reaction Conditions

Reaction Steps

0.30 g (0.93 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.24 g (2.80 mmol) of cyclopentylamine and 3 g of imidazole, and the mixture is heated under nitrogen at 145° C. for 4 h. The reaction product is removed from the flask by washing with ethanol, and the mixture is then treated with 10% hydrochloric acid and boiled until no more ethanol is present. The precipitated product is filtered off with suction, boiled in potassium carbonate solution and the solid residue is filtered off with suction and washed with hot dist. water. 60 mg (20%) of perylene-3,4-dicarboxylic anhydride can be recovered by acidifying the filtrate with conc. hydrochloric acid. The red residue is recrystallized 3 times by extraction with methanol and then dried in a drying cabinet at 120° C. Yield 0.22 g (61%) of dark-red small needles showing a strong red solid fluorescence, m.p. >315° C. Rf (CHCl3 /silica gel)=0.18. UV (CHCl3): λmax (ε)=506 (31013), 485 (31425) 355 (3050), 336 (3000), 319 (2680), 264 (34268), 256 (sh., 18100). Fluorescence (CHCl3): λmax (Irel)=541 (1), 572 (sh., 0.49).

Provenance & Evidence