Water → 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole

HRID 1803099노트

반응식

HRID 1803099 반응식
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18].[OH-].[K+].O>CS(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[O:17][CH3:18])[CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178478287HCID 178478287, 화합물

생성물 1

HCID 580753854-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole수율 42%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-09181f66b5f14e5c8845b555f7b439b5
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349880B2

반응 노트

불러오는 중…