Dimedone → HCID 12000661, compound

Participants

Reaction Steps

430 mg (1.76 mmol) of 5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde are combined to 197 mg (1.405 mmol) of dimedone, 335 mg (1.76 mmol) of 3-amino-2-ethoxycarbonylpyrrole hydrochloride, 742 mg (5.741 mmol) of N,N-diisopropylethylamine in 10 ml ethanol. The stirred reaction mixture is refluxed overnight. Upon cooling to room temperature, reaction mixture was half concentrated under reduced pressure and then diluted with water and extracted with ethyl acetate. The organic layer is washed with water and with brine and then dried on magnesium sulfate, filtered and concentrated under reduced pressure giving crude product. The resulting oily residue is dissolved in 10 ml of dichloromethane and purified by chromatography on a prepacked 120 g 15-40 μm silica gel cartridge (eluting solvent: cyclohexane/ethyl acetate from 100/0 to 70/30 v/v; rate: 50 mL/min, in 50 min, from 70/30 to 50/50 v/v in 10 min, and then from 50/50 to 40/60 v/v in 30 min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure giving 330 mg of expected compound with 47% yield.

Provenance & Evidence