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

HRID 1167469ノート

反応式

HRID 1167469 の反応式
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N: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:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1]

参加物

5

反応物 3

HCID 127492-MethylimidazoleHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

生成物 1

HCID 218766451-(2-fluoro-4-nitrophenyl)-2-methyl-1H-imidazole収率 52%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-Methylimidazole (9.02 g, 0.11 M) and N,N-diisopropylethylamine (32.2 g, 0.25 M) were dissolved in acetonitrile (160 ml), and 3.4-difluoronitrobenzene (15.9 g, 0.1 M) added. The mixture was stirred and heated to reflux under nitrogen for 24 hours. Solvent was evaporated, the residue dissolved in EtOAc (300 ml), washed with water (150 ml), brine (150 ml), and dried (magnesium sulfate). The residue was recrystallised from a mixture of EtOAc (25 ml) and cyclohexane (150 ml) with the addition of charcoal to give the title compound (11.5 g), mp 106-107°.

後処理

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 24 hours
  3. customSolvent was evaporated
  4. dissolutionthe residue dissolved in EtOAc (300 ml)
  5. washwashed with water (150 ml), brine (150 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customThe residue was recrystallised from a mixture of EtOAc (25 ml) and cyclohexane (150 ml) with the addition of charcoal

出典と根拠

ORDレコード
ord-91ed2fba17d7400ab306bc756c5b85c4
出典データセット
uspto-grants-2003_09
特許番号
US06617339B1

反応ノート

読み込み中…