Diisopropylethylamine → 1-(2-fluoro-4-nitrophenyl)-4-methyl-1H-imidazole

HRID 8155

반응식

HRID 8155 반응식
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(N(CC)C(C)C)(C)C.[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F>C(#N)C>[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178418800HCID 178418800, 화합물

생성물 1

HCID 218765961-(2-fluoro-4-nitrophenyl)-4-methyl-1H-imidazole

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-Methylimidazole (45.1 g, 0.55 M) and N,N-diisopropylethylamine (161 g, 1.25 M) were dissolved in acetonitrile (800 ml), and 3,4-difluoronitrobenzene (79.5 g, 0.5 M) added. The mixture was stirred and heated to reflux under nitrogen for 24 hours. Solvent was evaporated, the residue dissolved in ethyl acetate (800 ml), washed with water (400 ml), brine (200 ml), and dried (magnesium sulfate). The residue was dissolved in toluene (250 ml), treated with charcoal, filtered, and diluted with hot cyclohexane (75 ml) to crystallise 3-fluoro-4-(4-methylimidazol-1-yl)nitrobenzene (64.7 g).

후처리

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 24 hours
  3. customSolvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate (800 ml)
  5. washwashed with water (400 ml), brine (200 ml)
  6. dry with materialdried (magnesium sulfate)
  7. dissolutionThe residue was dissolved in toluene (250 ml)
  8. additiontreated with charcoal
  9. filtrationfiltered
  10. additiondiluted with hot cyclohexane (75 ml)
  11. customto crystallise 3-fluoro-4-(4-methylimidazol-1-yl)nitrobenzene (64.7 g)

출처 및 근거

ORD 기록
ord-dc7b9a5830914572958c7fec79e92c2d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087629B2

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