Benzyl Bromide → 1-Benzyl-3-(2-chloro-5-fluoro-phenyl)-5-isopropyl-imidazolidine-2,4-dione

Participants

Reaction Steps

This compound was synthesized in analogy to example 155 (step A to E). In step A, 2-methyl-propionaldehyde was starting material in place of cycloheptanone and ammonium acetate in place of cyclopropylamino acetate. In step B, 2-chloro-5-fluoro-phenyl amine was used in place of 4-Amino-benzoic acid ethyl ester. The pure 3-(2-chloro-5-fluoro-phenyl)-5-isopropyl-imidazolidine-2,4-dione that resulted from this procedure was then benzylated by stirring of 300 mg (1.11 mmol) of 3-(2-Chloro-5-fluoro-phenyl)-5-isopropyl-imidazolidine-2,4-dione with 141 ml (1.16 mmol) of benzyl bromide and 51 mg (1.16 ml) of sodium hydride (55% in oil) in 5 ml DMF for 3 h at RT. The reaction mixture was then taken up in ethyl acetate and was washed with 1N HCl and water. The crude product was purified by silica gel chromatography with Ethyl acetate/Heptane 1:3 to give 306 mg of pure 1-benzyl-3-(2-chloro-5-fluoro-phenyl)-5-isopropyl-imidazolidine-2,4-dione that was reduced with the same procedure described in step D and E to give pure 3-benzyl-1-(2-chloro-5-fluoro-phenyl)-4-isopropyl-imidazolidin-2-one as a colorless viscous oil MS (ESI): 347.3 (MH+).

Provenance & Evidence