Triethylamine → 4-(4-chloro-phenyl)-2-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-4,5-dihydro-1H-imidazole

HRID 1582465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582465
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:20])[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[NH2:10])=[CH:4][CH:3]=1.Cl.[CH3:22][O:23][C:24]1[CH:34]=[CH:33][C:27]([C:28](=N)OCC)=[CH:26][CH:25]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[NH:10][C:28]([C:27]3[CH:33]=[CH:34][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)=[N:20]2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 12270046Ethyl 4-methoxybenzimidate hydrochlorideHCID 227210671-(4-Chloro-phenyl)-2-(4-nitro-phenyl)-ethane-1,2-diamine

Produkt 1

HCID 1355308534-(4-chloro-phenyl)-2-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-4,5-dihydro-1H-imidazoleAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-chloro-phenyl)-2-(4-nitro-phenyl)-ethane-1,2-diamine (200 mg, 0.685 mmol) and ethyl 4-methoxy-benzimidate hydrochloride (148 mg, 0.686 mmol) in ethanol (5 mL) was added triethylamine (0.11 mL, 0.79 mmol). The reaction mixture was heated at reflux for 12 h. The solvent was removed to give a clear oil. It was then taken in methylene chloride (2 mL) and aqueous sodium carbonate. The product was extracted with methylene chloride (2×20 mL). The organic layers were washed with brine (1×5 mL), dried (Na2SO4) and concentrated. Purification of the crude residue by Biotage flash chromatography eluting with 70% ethyl acetate in hexanes gave 4-(4-chloro-phenyl)-2-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-4,5-dihydro-1H-imidazole (103 mg, 37%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed
  4. customto give a clear oil
  5. extractionThe product was extracted with methylene chloride (2×20 mL)
  6. washThe organic layers were washed with brine (1×5 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification of the crude residue by Biotage flash chromatography
  10. washeluting with 70% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-711ad68918dd4b8eb12008c1ca8a3bfa
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734302B2

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