N-Acetylimidazolidinone → Isaglidole

Participants

Reaction Steps

6.0 g (0.03 mol) of 2-amino-4-fluoro-isoindoline hydrochloride and 4.5 g (0.035 mol) of 1-acetyl-imidazolin-2-one are heated at 100° C. in 70 ml of phosphorus oxytrichloride for 4 hours. After removal of the POCl3 in vacuo, the residue is dissolved in 100 ml of ethanol and the solution is heated at the boiling point for 3 hours. The solvent is distilled off, 5N NaOH is added to the residue and the crude base is extracted with methylene chloride. Recrystallization from toluene gives 5.9 g of 4-fluoro-2-(2-imidazolin-2-ylamino)-isoindoline.

Provenance & Evidence