Potassium Hydroxide → HCID 60207316, compound

Participants

Reaction Steps

A solution of potassium hydroxide (72 mg, 1.27 mmol) in water (3.5 mL) was added to a suspension of ethyl 5-(2,3-dichlorophenylsulfanyl)-4-nitrothiophene-2-carboxylate (0.24 g, 0.63 mmol) in IMS (2 mL) and the resulting mixture was stirred at ambient temperature for 72 hours. After this time the mixture was diluted with water (4.5 mL) and washed the diethyl ether (2×5 mL). The aqueous phase was then acidified to pH 1 by the addition of 20% hydrochloric acid. The oil formed which solidified after stirring for 2 minutes. The mixture was left to stir for 1 hour then the solid was collected by filtration, washed with water (3×2 mL) and dried in vacuo at 40° C. overnight. The crude solid was absorbed onto silica and purified by chromatography over silica using ethyl acetate as eluent. The fractions containing the product were collected and the solvent removed under reduced pressure. The resulting solid was triturated with a small volume of diethyl ether, collected by filtration and dried in vacuo at 40° C. overnight to afford the title product as a yellow solid (58 mg, 26% yield). 1H NMR (d6-DMSO) δ: 8.08 (1H, s), 8.00 (2H, m), 7.64 (1H, m).

Provenance & Evidence