Sodium hydride → HCID 57006706, compound

Participants

Reaction Steps

A stirred mixture of 1-phenylmethylenamino-2-imidazolidinone (27.6 g, 0.1458 mole) [prepared as in Example A, Part II] in dimethylformamide (500 ml) is treated portionwise with 60% NaH in mineral oil (5.8 g, 0.1458 mole) over 30 minutes. The resulting mixture is stirred at ambient temperature 30 minutes, then heated at 80-90° C. for 30 minutes. The resulting thick mixture is cooled to ambient temperature, and 1-bromo-4-chlorobutane (50.0 g, 0.2916 mole, 2 eq) is added in one portion. The mixture is heated at 80°-90° C. After 30 minutes, a near-solution is formed followed, by gradual precipitation of a small amount of solid. The mixture is heated at 80°-90° C. temperature for 3 hours, then stirred at ambient temperature for 18 hours. The mixture is filtered (celite) removing a small amount of insoluble material. The filtrate is concentrated under reduced pressure to an oily residue. This residue is triturated with H2O giving a solid. The solid is collected and air-dried. This solid is triturated by stirring in anhydrous ether (350 ml) for one hour. The solid is collected and air-dried to give 36.4 g (0.130 mole) of 1-phenylmethyleneamino-3-(4-chlorobutyl)-2-imidazolidinone.

Provenance & Evidence