2-(2-chloro-5-nitrophenyl)-5-phenyl-1H-imidazole → 4-Chloro-3-(5-phenyl-1H-imidazol-2-yl) aniline

HRID 1505037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505037
[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>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

Komponenten

3

Edukt 1

HCID 580065202-(2-chloro-5-nitrophenyl)-5-phenyl-1H-imidazole

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-chloro-5-nitrophenyl)-5-phenyl-1H-imidazole (27 g, 90.3 mmol) in EtOH (200 ml) is added 5 nCl2.2H2O (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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0a9e2c336d86421f92c5cdeac8cd5c0c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216964B2

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