Water → HCID 3007459, compound

Participants

Reaction Steps

To a solution of 500 g (2.69 mol) of 2-[1-(1H-imidazol-1-yl)vinyl]phenol 4 in 3 L of DMSO was added 210 g (3.22 mol) of potassium hydroxide (pellet) with stirring and the mixture was stirred at room temperature for 1 hour. The solution was cooled to 12°-18° C. and there was dropwise added a solution of 577 g (2.95 mol) of 2,4-dichlorobenzyl chloride 9 in 100 ml of DMSO in 1 hour. The mixture was allowed to stand at the same temperature with stirring for 2 hours. To the reaction mixture was dropwise added 4.5 L of water with ice-cooling in 45 minutes. The resulting mixture was stirred for 1 hour, and the precipitating crystals were collected by filtration, washed with water (0.75 L×4) and then with n-hexane (0.7 L×3), and dried in air to give 872 g (yield: 94.1%) of the titled compound 10, m.p., 90.5°-93° C.

Provenance & Evidence