Diethyl Ether → HCID 10253281, compound

Participants

Reaction Steps

A stirred suspension of 2-hydroxy-5-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]benzoic acid (0.5 g, 1.26 mmol) and anhydrous potassium carbonate (0.36 g, 2.6 mmol) in anhydrous N,N-dimethylformamide (5 mL) was treated drop-wise at room temperature under nitrogen with a solution of iodoethane (0.405 g, 2.6 mmol) in anhydrous N,N-dimethylformamide (1 mL). The mixture was stirred at room temperature overnight. The reaction was diluted with diethyl ether and water. The organic phase was separated and washed sequentially with a 1 N hydrochloric acid solution and water. After drying over anhydrous sodium sulfate, the organic phase was filtered through a short column of silica gel, and the filtrate evaporated in vacuo to yield a crude product (0.5 g). The crude product was purified by preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with a mixture of methyl tert-butyl ether-hexane (15:85) at a flow rate of 40 mL/min to afford, after evaporation of the solvent, a colorless solid. Crystallization of the colorless solid from a mixture of diethyl ether-hexane yielded the title compound (0.239 g, 0.53 mmol, 42%) as a homogeneous, white powder, m.p. 113-115° C.;

Provenance & Evidence