Sodium hydride → HCID 21284128, compound

Participants

Reaction Conditions

Reaction Steps

13.5 g (0.07 mol) of 2-butoxy-6-ethylaniline are heated on a water separator with 11.8 g (0.099 mol) of ethyl glyoxylate in 100 ml of toluene until water formation is complete. The mixture is evaporated, the residue is dried in a high vacuum and taken up in 30 ml of dimethoxyethane, and the solution is added dropwise with 13.4 g (0.069 mol) of p-toluenesulfonylmethyl isocyanide to a suspension of 4.3 g (0.14 mol) of 80% strength sodium hydride (white oil) in 20 ml of dimethoxyethane at -20° C. When the gas evolution is complete, the mixture is hydrolyzed by adding water dropwise, the reaction products are extracted with methylene chloride, and the solvent is evaporated. The residue is taken up in 50 ml of ethanol, 20 g of potassium carbonate are added, and the mixture is stirred for 2 hours at 50° C. After evaporation, the residue is taken up in toluene/water, the organic phase is dried and evaporated, and the residue is chromatographed through a silica gel column (petroleum ether/ethyl acetate 8:2). 12.1 g (55% of theory relative to aniline employed) of ethyl 1-(2-butoxy-6-ethylphenyl)imidazole-5-carboxylate, a pale yellow oil, are obtained.

Provenance & Evidence