4-Morpholinobenzaldehyde → Ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate

HRID 1595367Notes

Reaction equation

HRID 1595367 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[N:15]O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.C([O-])(=O)C.[NH4+:36]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:36][C:28]([C:27]3[CH:30]=[CH:31][C:24]([N:21]4[CH2:22][CH2:23][O:18][CH2:19][CH2:20]4)=[CH:25][CH:26]=3)=[N:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2913494-MorpholinobenzaldehydeHCID 517165Ammonium AcetateHCID 178472894HCID 178472894, compound

Product 1

HCID 178470196Ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylateYield 24.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 3-(4-chlorophenyl)-2-hydroxyimino-3-oxopropionate (200 g), 4-morpholinobenzaldehyde (244.4 g) and ammonium acetate (603 g) were refluxed under heating for 15 hr in acetic acid, and the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform (2 L), and the solution was neutralized with a saturated aqueous hydrogencarbonate solution and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after drying, the solvent was evaporated under reduced pressure and crude crystals were obtained from ethyl acetate. The crude crystals were subjected to silica gel column chromatography to give the objective ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate (78 g), melting point 215° C.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform (2 L)
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customafter drying
  6. customthe solvent was evaporated under reduced pressure
  7. customcrude crystals were obtained from ethyl acetate

Sources & evidence

ORD record
ord-3ff0c9e84cce40eca2cca31ea61478fd
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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