反应详情

温度

100 °C

A mixture of 2-amino-4-(benzyloxy)-3-methoxybenzonitrile (144 g, 566 mmol) and sulfur (55 g, 1.7 mol) in ethylenediamine (800 mL) was degassed for 30 minutes then heated to 100° C. After 16 h the reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated under reduced pressure, diluted with a saturated sodium bicarbonate solution and extracted with EtOAc. The organic layer was washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The resulting solids were recrystallized from EtOAc and hexanes to afford 3-(benzyloxy)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxyaniline (145 g, 86%): 1H NMR (DMSO-d6) δ: 7.27-7.48 (5H, m), 7.14 (1H, d), 6.92 (2H, m), 6.64 (1H, m), 6.32 (1H, d), 5.11 (2H, s), 3.67 (3H, s), 3.33 (2H, s).

1. customwas degassed for 30 minutes
2. temperatureAfter 16 h the reaction mixture was cooled to room temperature
3. filtrationfiltered
4. concentrationThe filtrate was concentrated under reduced pressure
5. additiondiluted with a saturated sodium bicarbonate solution
6. extractionextracted with EtOAc
7. washThe organic layer was washed with brine
8. dry with materialdried (sodium sulfate)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe resulting solids were recrystallized from EtOAc and hexanes