p-Toluenesulfonic acid → HCID 15428634, compound

Participants

Reaction Steps

A mixture of 4-(1,3-dioxopentyl)benzenesulfonamide (160 mg, 0.63 mmol) of (Step 5), 4-fluoroaniline (65 μl, 0.69 mmol) and p-toluenesulfonic acid (6.7 mg) in toluene (25 ml) was heated at reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude mixture (820 mg) was purified by chromatography (silica gel, toluene/ethyl acetate, 8/2) to give 4-[1-(4-fluorophenyl)-5-methyl-1H-pyrrol-2-yl]benzenesulfonamide (92 mg, 45%) as a white solid: mp 147-48° C. Anal Calc'd. for C17H15N2FSO2 : C, 61.14; H, 4.65; N, 8.39; S, 9.60. Found: C, 61.34; H, 4.70; N, 8.21; S, 9.63.

Provenance & Evidence