反应详情

温度

80 °C

Step A (1): A mixture of 4-chloro-1H-imidazole (5.0 g, 48.8 mmol), 1-chloro-2-methoxy-4-nitrobenzene (9.15 g, 48.8 mmol), and potassium hydroxide flakes (2.74 g, 48.8 mmol) in anhydrous DMSO (50 mL) was heated at 80° C. for 20 h. The reaction mixture was allowed to cool to rt and was poured into 800 mL of water with vigorous stirring. The resulting yellow-orange precipitate was collected by vacuum filtration using a coarse sintered glass funnel. The crude wet solid was transferred to a 1 L Erlenmeyer flask. Absolute ethanol (250 mL) was added to the flask and the resulting suspension was heated until all of the solids dissolved. The clear solution was cooled to rt and the desired product slowly crystallized. After 2 h, the crystalline solid was collected by vacuum filtration and rinsed with 100 mL of fresh ethanol. The solid was dried under high vacuum to afford 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole (5.2 g, 42% yield) as an off-white crystalline solid. LC-MS (M+H)+=254.0. 1H NMR (500 MHz, chloroform-d) δ ppm 7.94-8.01 (m, 2 H) 7.76 (d, J=1.53 Hz, 1 H) 7.45 (d, J=8.55 Hz, 1 H) 7.21 (d, J=1.53 Hz, 1 H) 4.02 (s, 3 H).

1. temperatureto cool to rt
2. filtrationThe resulting yellow-orange precipitate was collected by vacuum filtration
3. additionAbsolute ethanol (250 mL) was added to the flask
4. temperaturethe resulting suspension was heated until all of the solids
5. dissolutiondissolved
6. temperatureThe clear solution was cooled to rt
7. customthe desired product slowly crystallized
8. filtrationthe crystalline solid was collected by vacuum filtration
9. washrinsed with 100 mL of fresh ethanol
10. customThe solid was dried under high vacuum