3,5-Dichlorophenyl isocyanate → 3-(3,5-Dichlorophenyl)-5-methyl-1-(prop-2-yn-1-yl)imidazolidine-2,4-dione

Participants

Reaction Steps

To a solution of 10 g (0.07 mole) of methyl 2-propargylaminopropionate in 100 ml of toluene with 2 drops of stannous octoate is added 14.5 g (0.077 mole) of 3,5-dichlorophenylisocyanate in small portions. The resulting mixture is heated at 100° for 3 hours. It is then washed with water twice and dried over sodium sulfate. Solvent is evaporated to give a thick yellow oil. Material is further purified by passing it through a silica gel column using 30/70 ethyl acetate/hexane as solvent to give 18 g of a light yellow oil which solidifies on standing. The solids are triturated in boiling hexane and collected by filtration, mp 105°-6°. NMR and elemental analysis confirm the desired structure.

Provenance & Evidence