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

HRID 475716

반응식

HRID 475716 반응식
[CH3:1][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>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178418800HCID 178418800, 화합물

생성물 1

HCID 454801801-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazole수율 20.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
110 °C

실험 절차

A mixture of 4-methyl-1H-imidazole (18.0 g, 53.5 mmol), 1-chloro-2-methoxy-4-nitrobenzene (10.0 g, 53.5 mmol), and potassium hydroxide (4.5 g, 80.3 mmol) in DMSO (50 mL) was heated at 110° C. for 24 h. The reaction mixture was allowed to cool to rt and was poured into 1000 mL of water. The aqueous mixture was extracted with dichloromethane (3×250 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel chromatography (330 g silica cartridge, 0-2% MeOH/chloroform, linear gradient over 72 min, flow 25 mL/min) to afford 1-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazole (2.56 g, 20% yield) as a yellow/orange solid. LC-MS (M+H)+=234.1. 1H NMR (500 MHz, CDCl3) δ ppm 7.97-8.00 (m, 1H) 7.93-7.97 (m, 2H) 7.45 (d, J=8.85 Hz, 1H) 7.02 (s, 1H) 4.02 (s, 3H) 2.35 (s, 3H).

후처리

  1. temperatureto cool to rt
  2. extractionThe aqueous mixture was extracted with dichloromethane (3×250 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customwas purified
  9. customsilica gel chromatography (330 g silica cartridge, 0-2% MeOH/chloroform, linear gradient over 72 min, flow 25 mL/min)

출처 및 근거

ORD 기록
ord-ca0ee2577273421dbefc3b77a3674f24
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637525B2

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