反应详情

温度

130 °C

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.

1. temperaturecooled to room temperature
2. washthe solution was washed several times with isopropyl ether
3. extractionThe product was extracted three times into isopropyl ether
4. washwashed twice with water and once with a saturated sodium chloride solution
5. dry with materialdried (sodium sulfate)
6. filtrationfiltered
7. customevaporated to a liquid that
8. additionwas added to water (3L)
9. extractionextracted into three portions of isopropyl ether
10. washThe combined extracts were washed twice with water and once with a saturated sodium chloride solution
11. dry with materialdried (magnesium sulfate)
12. additiontreated with charcoal
13. filtrationfiltered
14. customevaporated under reduced pressure to a liquid (91.4 g)
15. dissolutionA 6.0 g portion was dissolved in isopropanol
16. additiona solution of oxalic acid (3.1 g) in isopropanol was added
17. filtrationThe resulting solid was collected by filtration
18. washrinsed with isopropyl ether