Water → HCID 86591957, compound

Participants

Reaction Steps

To a solution of 3-(N-tert-butoxycarbonylmethylamino)benzoic acid (10.0 g, 39.8 mmol) in 100 mL of tetrahydrofuran was added carbonyl diimidazole (6.78 g, 41.8 mmol) under Argon. After 2 h of stirring, diethylamine (5.82 g, 79.4 mmol) was added, and the reaction mixture was stirred for 18 h and then refluxed 3 h. After cooling, water (50 mL) was added to the reaction flask, and the contents were concentrated on a rotary evaporator. The resulting mixture was extracted three times with dichloromethane (50 mL). These extracts were combined, washed twice with 1 N aqueous hydrochloric acid solution (50 mL) and twice with water (50 mL), dried (Na2SO4), and concentrated to give 11.9 g (98%) of N,N-diethyl 3-(N-tert-butoxycarbonylmethylamino)benzamide as a yellow oil. MS (ES), m/z 307 (MH+). 300 MHz 1H NMR (CDCl3) δ1.03-1.19 (br m, 3H), 1.15-1.30 (br m, 3H), 1.45 (s, 9H), 3.14-3.31 (br m, 2H), 3.45-3.62 (br m, 2H), 4.33 (d, J=5.6 Hz, 1H), 4.95 (br s, 1H), 7.19-7.38 (m, 4H).

Provenance & Evidence