Dichloromethane → HCID 18367272, compound

Participants

Reaction Steps

A mixture of benzoin (45.19 g, 0.21 mol), pyroglutamic acid (25.00 g, 0.19 tool), DCC (47.91 g, 0.23 mol), DMAP (catalytic quantity) and CH2Cl2 (600 mL) was stirred at room temperature. After about 7 hours, the mixture was filtered, concentrated and diluted with AcOH (650 mL). NH4OAc (75.00 g, 0.97 mol) was added and the mixture heated at reflux for about 1.25 hours before being cooled, diluted with H2O and extracted with CH2Cl2. The combined extracts were washed with H2O (3 times), dried over Na2SO4 and concentrated in vacuo to give a yellow solid. Chromatography on a column of silica gel using a mixture of CHCl3 and MeOH (99:1) as eluent afforded 5-(4,5-diphenyl-2-oxazolyl) -2-pyrrolidinone (42.58 g, 72%). An analytical sample was recystallised from CH2Cl2 and hexanes and had mp 145-147° C. IR (KBr)1700 (NH.CO) cm-1 ; 1H NMR (DMSO-d6) δ2.15-2.60 (4H, m, CH2), 4.89 (1H, m, CHN), 7.10-7.70 (10H, m, aromatic H), 8.33 (1H, s, NH); MS m/z 305 (MH+).

Provenance & Evidence