Stannous chloride dihydrate → 4-Chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline

HRID 1890725ノート

反応式

HRID 1890725 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[NH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:15]=1.O.O.Cl[Sn]Cl>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[NH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:15]=1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 580065202-(2-chloro-5-nitrophenyl)-5-phenyl-1H-imidazole

生成物 1

HCID 498408204-Chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-(2-chloro-5-nitrophenyl)-5-phenyl-1H-imidazole (27 g, 90.3 mmol) in EtOH (200 ml) is added SnCl2.2H2O (71 g, 316 mmol). The mixture is refluxed for 2 hours, cooled to room temperature and then concentrated. Ethyl acetate (200 ml) and NaOH (25 g in 100 ml water) are added to the residue and the mixture is stirred for 10 minutes at room temperature. The solid is removed by filtering through celite pad. The filtrate is separated and the organic layer is further washed with brine, dried over anhydrous MgSO4 and concentrated. The crude product is purified by silica gel flash chromatography, eluted with 40% ethyl acetate in dichloromethane to afford 4-Chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline as a brown solid. LC-MS m/z: 270.1 (M+1).

後処理

  1. temperatureThe mixture is refluxed for 2 hours
  2. concentrationconcentrated
  3. additionEthyl acetate (200 ml) and NaOH (25 g in 100 ml water) are added to the residue
  4. customThe solid is removed
  5. filtrationby filtering through celite pad
  6. customThe filtrate is separated
  7. washthe organic layer is further washed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated
  10. customThe crude product is purified by silica gel flash chromatography
  11. washeluted with 40% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-1350a8faf49d44468027a67e180fb439
出典データセット
uspto-grants-2013_08
特許番号
US08507491B2

反応ノート

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