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

HRID 1803099ノート

反応式

HRID 1803099 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178478287HCID 178478287、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-09181f66b5f14e5c8845b555f7b439b5
出典データセット
uspto-grants-2013_01
特許番号
US08349880B2

反応ノート

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