Triethylamine → HCID 86662102, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-(3-chloro-2-thienyl)-3-oxopropanoate (1.26 g, 5.42 mmol) was dissolved in anhydrous acetonitrile (10 mL), treated with triethylamine (0.63 mL, 6.2 mmol, 1.15 equiv) and cooled to 0° C. To the mixture was added 4-acetamidobenzenesulfonyl azide (1.43 g, 6.0 mmol, 1.1 equiv) and after 10 minutes at 0° C., the mixture was warmed to ambient temperature. To the mixture, additional acetonitrile (20 mL) was added and the mixture was stirred at ambient temperature for an additional 45 minutes. The mixture was treated with sodium hydroxide (10 mL, 1 N aqueous), sodium carbonate (25 mL, aqueous saturated) and water (75 mL) and then extracted with ethyl acetate (2×150 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 70:30; hexanes:ethyl acetate), providing the titled compound.

Provenance & Evidence