Sodium hydride → HCID 70173102, compound

Participants

Reaction Conditions

Reaction Steps

1-Phenylmethylenamino-3-(4-chlorobutyl)-2,4-imidazolidinedione dihydrochloride is prepared by adding 60% sodium hydride in mineral oil (7.8 g, 0.1944 mole) over 1 hour to a stirred solution of 1-(benzylideneamino)hydantoin [prepared as described by J. Gut, A Novacet, and P. Fiedler, Coll. Czech. Chem. Commun., Vol. 33, pp. 2087-2096 (No. 7). 1968 hereby incorporated by reference herein] (39.5 g, 0.1944 mole) in dimethylformamide (1000 ml). After complete addition, the solution is heated at steam bath temperature (approximately 100° C.) for 1.5 hours. The resulting mixture is allowed to cool to ambient temperature (30° C.). While stirring at ambient temperature, 1-bromo-4-chlorobutane (100 g, 0.5832 mole, 3 eq) is added in one portion. The mixture becomes exothermic reaching around 35° C. in approximately 30 minutes. The near-solution is heated at approximately 80° C. by steam bath for four hours, cooled and stirred for approximately eight hours at ambient temperature (30° C.). The cloudy mixture is filtered, removing a small amount of insoluble solid. The filtrate is concentrated under reduced pressure to a semi-solid residue. This residue is triturated with H2O (400 ml), collected, recrystallized from acetonitrile, and then air-dried to give 43.1 g (0.1467 mole) of 1-phenylmethyleneamino-3-(4-chlorobutyl)-2,4-imidazolidinedione.

Provenance & Evidence