Sodium Carbonate → 2-Phthalimidoacetamide

Participants

Reaction Steps

To a stirred solution of glycinamide hydrochloride (2.20 g, 20.0 mmol) and sodium carbonate (2.54 g, 24 mmol) in 25 mL of water is added N-carbethoxyphthalimide (4.38 g, 20.0 mmol). The resulting suspension is stirred for 1.5 hour and then filtered to afford 3.22 g (79%) of crude product as a white powder. The crude product is slurried in 200 mL of refluxing ethanol and, after cooling to room temperature, the resulting suspension is filtered and the solid dried in vacuo (60° C., <1 mm) to afford 2.65 g (65%) of N-phthaloylglycinamide, which can be alternatively named as phthalimidoacetamide, as a white powder: mp 199°-201° C.; 1H NMR (dmso-d6) δ 8.00-7.8 (m, 4 H, Ar), 7.70 (br s, 1 H, CONH2), 7.26 (br s, 1 H, CONH2), 4.16 (s, 2 H, CH2); 13C NMR (dmso-d6) δ 167.8, 167.5, 134.4, 131.7, 123.1, 39.9. Anal. Calculated for C11H10N2O3. Theoretical: C, 60.55; H, 4.62; N, 12.84. Found: C, 60.49; H, 4.59; N, 12.82.

Provenance & Evidence