Dichloromethane → n-(2-Oxo-2-phenylethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

2-oxo-2-phenylethanaminium chloride (5) (1.7 g, 10.0 mmol, 1.0 equiv.) was added to a 100 mL RBF followed by CH2Cl2 (50 mL). The resulting solution was cooled to 0° C. via an ice bath. Next, acetic anhydride (1.4 mL, 15.0 mmol, 15.0 equiv.) and DIEA (5.3 mL, 30.0 mmol, 30.0 equiv.) were added to the reaction flask. The reaction solution stirred for 2 h at 0° C. and was allowed to warm to rt. The solution was stirred at rt for 1 h. The solution was transferred to a separatory funnel with CH2Cl2 (90 mL). The resulting organic layer was washed with 1% HCl (2×50 mL) and sat. NaCl (2×50 mL). The organic layer was dried over Na2SO4, concentrated on a rotary evaporator, and dried under vacuum to give a yellowish solid. The solid was dissolved in EtOAc (15 mL) and precipitated during the slow addition of hexanes (30 mL). The precipitate that formed was dried under vacuum to give 1.3 g (74%) of 10 as a white solid. Rf=0.31 (100% EtOAc); mp=85-87° C.; IR (KBr) 3319, 3059, 2936, 2900, 1683, 1649, 1597, 1556, 1370, 1011 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.98 (d, J=7.5 Hz, 2H, Ph-H), 7.63 (t, J=7.5 Hz, 1H, Ph-H), 7.50 (t, J=7.5 Hz, 2H, Ph-H), 6.69 (br s, 1H, Ac—NH), 4.78 (d, J=4.5 Hz, 2H, Ac—NH—CH2), 2.12 (s, 3H, NH—COCH3); 13C NMR (125 MHz, CDCl3) δ 194.4, 170.5, 134.5, 134.3, 129.1, 128.1, 46.7, 23.2; LRMS (ESI-MS m/z): Mass calcd for C10H11NO2 [M]+, 177.20. Found 178. Anal. calcd for C10H11NO2: C, 67.78; H, 6.26; N, 7.90 Found: C, 67.63; H, 6.29; N, 7.87. Spectroscopic data were consistent with the literature data for this compound.

Provenance & Evidence