Ethanol → HCID 43445089, compound

HRID 2356700Notes

Reaction equation

HRID 2356700 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:15]([O:17]CC)=[O:16])[CH3:2].[OH-].[Na+].C(O)C>O1CCCC1>[CH2:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:15]([OH:17])=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 67546823HCID 67546823, compound

Product 1

HCID 43445089HCID 43445089, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-ethyl-2-(4-fluorophenyl)imidazol-4-carboxylate (2.81 g), 4N aqueous sodium hydroxide solution (14 ml), ethanol (35 ml) and tetrahydrofuran (15 ml) was stirred at room temperature overnight, followed by refluxing for 3 hours. 4N aqueous sodium hydroxide solution (28 ml) was added to the mixture and the mixture was refluxed overnight. After cooling, the reaction mixture was concentrated under reduced pressure and neutralized by 10% hydrochloric acid, and precipitated solid was collected by filtration. The solid was dissolved in tetrahydrofuran, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was triturated with diethyl ether to obtain first crop of 5-ethyl-2-(4-fluorophenyl)imidazol-4-carboxylic acid (1.06 g) as colorless powder. Moreover, the filtrate was purified by HP-20 resin (trade name, available from Nippon Rensui K.K.) (solvent: water→methanol) to give second crop of 5-ethyl-2-(4-fluorophenyl)imidazol-4-carboxylic acid (1.60 g).

Workup

  1. temperatureby refluxing for 3 hours
  2. temperaturethe mixture was refluxed overnight
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customprecipitated solid
  6. filtrationwas collected by filtration
  7. dissolutionThe solid was dissolved in tetrahydrofuran
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8b4e2c0802e14024b426e6d43eb9d291
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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