Sodium hydride → HCID 54152133, compound

Participants

Reaction Steps

A solution of 4-chloro-4'-trifiuoromethyls ulfonyloxybenzophenone-N-ethoxycarbonylhydrazone (0.5 g) in tetrahydrofuran (6 ml) was stirred at room temperature under a nitrogen atmosphere, during which an oily mixture (50 mg) of sodium hydride containing 60% (w/w) sodium hydride was added to the solution at a time. After stirring at room temperature for 15 minutes and finding no evolution of hydrogen gas, the mixture was cooled to -78° C., and chloro-{N-(2-ethoxycarbonylethyl)-N-isopropylamino }sulfide (0.3 g) was added dropwise over 3 minutes. The reaction mixture was warmed to room temperature over 4 hours, and then poured into ice-water. Further, a saturated saline solution was added thereto. The aqueous layer was extracted with ethyl acetate, and the extract was combined with the organic layer. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography, which afforded 0.2 g of 4-chloro-4'-trifluoromethylsulfonyloxybenzo- phenone-N-ethoxycarbonyl-N-{N'-(2-ethoxycarbonylethyl)-N'-isopropylaminosulfenyl }-hydrazone (compound 28).

Provenance & Evidence