N,N'-Dimethylethylenediamine → 2-chloro-N-(4-(5-methyl-2-phenyloxazol-4-yl)phenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of potassium carbonate (0.898 g, 6.50 mmol), copper(I) iodide (0.0309 g, 0.162 mmol), 2-chlorobenzamide (0.607 g, 3.90 mmol) and 4-(4-bromophenyl)-5-methyl-2-phenyloxazole (1.021 g, 3.25 mmol) in 10 mL 1,4-dioxane was added N,N′-dimethylethylenediamine (0.0350 ml, 0.325 mmol). The reaction was purged with nitrogen twice (evacuated-backfill) then heated in a 110° C. oil bath. After ca. 72 h the reaction was filtered and the filtrate concentrated under reduced pressure. The concentrate was triturated several times with ethyl acetate and the collected solid was discarded. The product was purified from the filtrate by chromatography on silica gel, eluting with 20-60% ethyl acetate in hexane, to afford product as a faintly yellow solid. ESI+ m/z=389.0 [MH]+.

Provenance & Evidence