Dimethylformamide → HCID 86623507, compound

Participants

Reaction Conditions

Reaction Steps

To a 5 L-three neck flask equipped with a mechanic stirrer, heating mantle with temperature controller and a gas outlet, were charged N-hydroxysuccinimide (426 g, 3.7 mol), 2-chloro-5-chloromethylpyridine (500 g, 3.1 mol) and anhydrous DMF (1 L). The mixture was stirred for 5 min when inner temperature dropped to 8.5° C. Anhydrous K2CO3 (640 g, 4.6 mol) was charged in one portion followed by anhydrous DMF (0.5 L). It was stirred for 5 min when inner temperature raised to 15.5° C. The mixture was heated to 70° C. (preset) within 30 min but the temperature continued to rise to 89° C. over 1 h of reaction period, during which a lot of gas was evolved and the reaction was finished as judged by MS and TLC, or simply the termination of gas-evolving. It was cooled down to room temperature, poured into water (6 L) with mechanic stirring. The insoluble was collected by filtration and washed with water (1.5 L), air-dried for 60 h to give the desired product as an off-white powder (364 g, 49%). ESIMS m/e (M+H)+: 241. 1H NMR (500 MHz, CDCl3): 8.44 (s, 1H), 7.95 (d, 1H, 3J=8.5 Hz), 7.41 (d, 1H, 3J=8.0 Hz), 5.14 (s, 2H), 2.73 (s, 4H) ppm. 13C NMR (125 MHz, CDCl3): δ 170.8, 152.6, 150.2, 140.2, 128.2, 124.4, 74.9, 25.4.

Provenance & Evidence