Chlorosuccinimide → HCID 20363323, compound

Participants

Reaction Steps

A mixture of 14.60 g. (0.04 mole) of the 2-(2',6'-dichlorophenyl)-4,5-diphenylimidazole, 5.34 g. (0.04 mole) of N-chlorosuccinimide, and 400 ml of carbon tetrachloride was heated at reflux temperature for 2 hours. The solution was cooled, filtered, and thefiltrate concentrated under vacuum. The resulting solid-oil mixture was triturated with 1-chlorobutane to give a residue of 16.68 g., m.p. 120°-140° C. (broad). The compound proved difficult to recrystallize from common solvents and only acetonitrile and nitromethane afforded reasonable recovery of crystals; from the latter solvents the crystals formed as large chunky aggregates. The best fraction 0.7664 g. has m.p. 125°-127° C.; an IR spectrum showed no NH absorption and a very strong 1620 cm-1 band.

Provenance & Evidence