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

HRID 1582465Notes

Reaction equation

HRID 1582465 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-711ad68918dd4b8eb12008c1ca8a3bfa
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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