Iodine → HCID 54423472, compound

Participants

Reaction Steps

To a stirred solution of 1-phenyl-2-(4-methylthiophenyl)-1-buten-3-one oxime (Step 2) (11.2 g, 0.0395 mol), sodium bicarbonate (13.6 g, 0.162 mol), and potassium iodide (22.95 g, 0.138 mol) in tetrahydrofuran (200 ml) and water (160 ml) was added iodine (10 g, 0.0395 mol). The reaction vessel was covered with aluminum foil and heated at reflux for 4 hours. Thin layer chromatography indicated the reaction was completed. The reaction was cooled to room temperature, sodium bisulfite was added and the reaction was extracted with ethyl acetate. The organic extracts were dried and the solvent was removed to give the crude isoxazole. The crude was purified by chromatography on silica gel using mixtures of ethyl acetate and toluene. The isoxazole was recrystallized from ethyl acetate and hexane to give pure compound as a crystalline solid (8.3 g, 75%): mp 88°-90° C. Anal. Calc'd. for C17H15NOS (281.38): C, 72.57; H, 5.37; N, 4.98; S, 11.40. Found: C, 72.20; H, 5.27; N, 4.58; S, 11.69.

Provenance & Evidence