Water → HCID 178424018, compound

HRID 1595317Notes

Reaction equation

HRID 1595317 reaction equation
[CH:1]1([C:7]2[NH:8][C:9]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[C:10]([C:12]([O:14]C)=[O:13])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].O>C(O)C>[CH:1]1([C:7]2[NH:8][C:9]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[C:10]([C:12]([OH:14])=[O:13])[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 178499063HCID 178499063, compound

Product 1

HCID 178424018HCID 178424018, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-cyclohexyl-5-(4-methylphenyl)imidazole-4-carboxylate (900 mg) was dissolved in ethyl alcohol (20 ml). Lithium hydroxide hydrate (1.1 g) and water (10 ml) were added, and the mixture was refluxed under heating for 2.5 hr and concentrated under reduced pressure. To the obtained residue were added water and ethyl acetate, and the mixture was partitioned. The aqueous layer was filtered, and aqueous citric acid was added to the filtrate. The precipitated crystals were collected by filtration to give 2-cyclohexyl-5-(4-methylphenyl)imidazole-4-carboxylic acid (390 mg), melting point 205-206° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2.5 hr
  3. concentrationconcentrated under reduced pressure
  4. additionTo the obtained residue were added water and ethyl acetate
  5. customthe mixture was partitioned
  6. filtrationThe aqueous layer was filtered
  7. additionaqueous citric acid was added to the filtrate
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-c47d62240391412e84682b50229163e2
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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