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

HRID 1890725노트

반응식

HRID 1890725 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1350a8faf49d44468027a67e180fb439
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507491B2

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