Sodium hydride → HCID 70254767, compound

Participants

Reaction Steps

3.1 g (0.0112 mole) of N-(4'-trifluoromethylsulfinyl-phenyl)-cyanoacetamide in 100 ml of anhydrous THF and 10 mg of catalytic imidazole and 0.75 g (0.0246 mole) of sodium hydride (80% oil dispersion) were stirred at room temperature for 90 minutes and then 1.32 ml (0.0146 mole) of cyclopropylcarbonyl chloride were added dropwise. The solution was stirred at room temperature for 10 minutes, was poured into a 1M HCl/water mixture and was filtered. The product was dissolved in dichloromethane and chromatographed on a short silica column (dichloromethane) to obtain 2.54 g (66% yield) of N-(4'-trifluoromethylsulfinyl-phenyl)-2-cyano-3-cyclopropyl-3-hydroxy-prop-2-enamide melting at 155°-157° C.

Provenance & Evidence