Ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate → HCID 178524860, compound

HRID 1595368Notes

Reaction equation

HRID 1595368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:25]([O:27]CC)=[O:26])=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:25]([OH:27])=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178470196Ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate

Product 1

HCID 178524860HCID 178524860, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate (53.7 g) was dissolved in ethanol (540 ml) and 3N aqueous sodium hydroxide solution (217 ml), and the mixture was refluxed under heating for 5 hr and concentrated under reduced pressure. Water (100 ml) was added and the mixture was washed with toluene. The aqueous layer was neutralized with 10% aqueous citric acid solution and the precipitated crystals were collected by filtration to give the objective 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxyic acid (49.4 g), melting point 205° C. (decomposition).

Workup

  1. temperatureunder heating for 5 hr
  2. concentrationconcentrated under reduced pressure
  3. additionWater (100 ml) was added
  4. washthe mixture was washed with toluene
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-83d7bcf095df4576b78a1796c87f791e
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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