Hydrochloric Acid → HCID 22400396, compound

Participants

Reaction Steps

The above hydrochloride was converted to the free base in ether with 5% sodium bicarbonate solution. To a suspension of sodium hydride (57 mg, 2.38 mmol) in dimethylformamide (3 mL) held at 0° C. under argon was added a solution of diethyl malonate (0.4 g, 2.5 mmol) in dimethylformamide (3 mL). The mixture was stirred at ambient temperature for 0.5 hour or until a clear solution resulted. Then, 5-(2-chloroethyl)-1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazole (0.61 g, 1.85 mmol) in dimethylformamide (5 mL) was added, and the mixture was heated at 95° C.-100° C. for 24 hours. The reaction was partitioned between water and ethyl acetate, and the organic layer was washed with water, dried, concentrated and the residue chromatographed to provide 0.6 q (71%) of diethyl 2-[1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl]ethylmalonate as an oil.

Provenance & Evidence