Sodium hydride → HCID 3775915, compound

Participants

Reaction Steps

A suspension of NaH (80% in paraffin) (3.97 g; 0.165 moles) in anhydrous ethyl ether (100 ml), maintained under nitrogen stream, is dropwise added with a solution of 3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (18.11 g; 0075 moles) and tosylmethylisocianide (TOSMIC) (14.60 g; 0.075 moles) in anhydrous dimethylsulfoxide (170 ml) diluted with anhydrous ethyl ether (300 ml). Upon the additions are completed, the mixture is maintained under stirring at room temperature for 3 hours. After dilution with water (800 ml) the precipitate is filtered, washed with absolute ethanol and lastly with petroleum ether. There are obtained 10.40 g (yield 49.4%) of 4-benzoyl-3-(4-chlorophenyl)-1H-pyrrole, which is crystallized from N,N-dimethylformamide and water (m.p.: 232°-235° C.).

Provenance & Evidence