Ammonium Hydroxide → HCID 21250949, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-phthaloylglycine (2.50 g, 8.89 mmol) in tetrahydrofuran (50 mL) is added carbonyldiimidazole (1.50 g, 9.25 mmol) and a few crystals of 4-N,N-dimethylaminopyridine. The reaction is then heated to 50° C. for 45 minutes. After the reaction mixture had cooled to room temperature, 1 mL of concentrated ammonium hydroxide is added via syringe. The reaction is stirred for 1 hour, then diluted with 50 mL of water and partially concentrated to remove the majority of the tetrahydrofuran. The resulting slurry was filtered and the solid washed with copious amounts of water. The solid was dried in vacuo (60° C., <1 mm) to afford 1.9 g (76%) of α-phthalimidophenylacetamide as an off-white powder: mp 218°-220° C.; 1H NMR (DMSO-d6) δ 9.00-7.75 (m, 4 H, Ar), 7.61 (br s, 1 H, CONH2), 7.55-7.20 (m, 6 H, Ar, CONH2), 5.82 (s, 1 H, CHCO2); 13C NMR (DMSO-d6) δ 168.2, 167.1, 135.6, 134,5, 131.4, 129.4, 127.9, 127.7, 123.1, 56.3.

Provenance & Evidence