Potassium Iodide → HCID 19811458, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tetrahydrofurfuryl chloride (100 g, 0.829 mol), aniline (2.09 g, 2.25 mol) and potassium iodide (1.0 g) was heated at 130° C. under nitrogen for 36 hours and cooled to room temperature. A 3N hydrochloric acid solution (400 mL) was added and the solution was washed several times with isopropyl ether and made basic with a 50% sodium hydroxide solution. The product was extracted three times into isopropyl ether, washed twice with water and once with a saturated sodium chloride solution, dried (sodium sulfate), filtered and evaporated to a liquid that was added to water (3L) and extracted into three portions of isopropyl ether. The combined extracts were washed twice with water and once with a saturated sodium chloride solution, dried (magnesium sulfate), treated with charcoal, filtered and evaporated under reduced pressure to a liquid (91.4 g). A 6.0 g portion was dissolved in isopropanol and a solution of oxalic acid (3.1 g) in isopropanol was added. The resulting solid was collected by filtration and rinsed with isopropyl ether to give 6.3 g of solid. A 1.5 g portion was recrystallized from isopropanol/isopropyl ether/light pet ether to give a solid that was removed by filtration. A second crop of crystals was obtained from the filtrate, dried under high vacuum at 60° C. to give 0.31 g, mp 149°-156° C.

Provenance & Evidence