Hydrochloric Acid → HCID 59707063, compound

Participants

Reaction Steps

Sodium hydride (approximately 60% strength suspension in oil, 140 mg, approximately 3.5 mmol) was added portionwise to a solution of 1-(4-tert-butylbenzyl)imidazolidin-2-one (C) (730 mg, 3.15 mmol) in abs. DMF (15 mL) under a blanket of argon within a period of 10 min. The reaction mixture was stirred for 60 min at RT and a solution of 2-(4-bromomethylphenyl)-isoindol-1,3-dione (B) (1 g, 3.16 mmol) in abs. DMF (20 mL) was then added within a period of 60 min. The reaction mixture was stirred at RT over a period of 3 h, then heated to 100° C. over a period of 1 h, cooled, and added to a mixture of ice water (300 mL) and 2N hydrochloric acid solution in H2O (20 mL). The resulting mixture was stirred for 30 min and then extracted with DCM (4×20 mL). The combined organic phases were dried over Na2SO4 and the solvent removed in vacuo. Following purification, by column chromatography, of the residue (SiO2, cyclohexane/EtOAc 1:1), the desired product 2-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}isoindol-1,3-dione (E) was obtained as vitreous solid matter (680 mg, 46% of theory).

Provenance & Evidence