3-(2-Chloroethyl)-1,3-oxazolidin-2-one → HCID 131714810, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5.1 g (0.012 mol) of N-[2-(acetyloxy)ethyl]-N-[2-(5-amino-2H[1]benzothiopyrano[4,3,2-cd]indazol-2-yl)ethyl]acetamide, hydrochloride salt and 11.6 g (0.077 mol) of 3-(β-chloroethyl)-2-oxazolidinone was stirred at 150° C. for 2 hours, dissolved in 20 ml of a CH2Cl2 /MeOH (20/1) mixture, and flash chromatographed over silica gel, eluting with a CH2Cl2 /MeOH (20/1) mixture. The appropriate fractions were combined and concentrated to dryness in vacuo. The residue was treated with 20 ml of 2N KOH in MeOH, 10 ml of H2O, and 10 ml of THF, and the mixture was heated under reflux under a N2 atmosphere for 16 hours. The mixture was treated with 100 ml of H2O and 100 ml of CH2Cl2 and the layers were separated. The aqueous phase was extracted twice with CH2Cl2 and the Ch2Cl2 extracts were combined, dried (MgSO4), and concentrated to dryness in vacuo. The residue was dissolved in 50 ml of EtOH and treated with an excess of i-PrOH saturated with gaseous HCl. The precipitate was collected and recrystallized from MeOH to give 6.0 g of product, mp 222°-225° C.

Provenance & Evidence