HCID 19815328, compound → HCID 19815363, compound

HRID 653913Notes

Reaction equation

HRID 653913 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[O:7][C:8]1[CH:26]=[CH:25][C:11]([CH2:12][N:13]2[C:17]([CH2:18][OH:19])=[C:16]([Cl:20])[N:15]=[C:14]2[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:10][CH:9]=1)([O:3]C)=[O:2]>C(O)C.[OH-].[Na+]>[CH2:21]([C:14]1[N:13]([CH2:12][C:11]2[CH:25]=[CH:26][C:8]([O:7][C:6]3[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=3[C:1]([OH:3])=[O:2])=[CH:9][CH:10]=2)[C:17]([CH2:18][OH:19])=[C:16]([Cl:20])[N:15]=1)[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 1

HCID 19815328HCID 19815328, compound

Product 1

HCID 19815363HCID 19815363, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 7.70 g of 1-[4-(2-carbomethoxyphenoxy)benzyl]-2-butyl-4-chloro-5-hydroxymethyl imidazole in 250 mL of ethanol and 125 mL of 10% aqueous sodium hydroxide was refluxed for 5 hours. After cooling, the reaction mixture was filtered, and the solvent was removed in vacuo. The residue was dissolved in water, and the solution was acidified to pH 3.5 using hydrochloric acid. The precipitated solid was recovered by filtration and recrystallized from acetone to furnish 6.52 g of 2-butyl-4-chloro-1-[4-(2-carboxyphenoxy)benzyl]-5-hydroxymethylimidazole, m.p. 178°-180°. NMR (200 MHz, DMSO) δ 7.79 (d, 1H); 7.53 (t, 1H); 7.23 (t, 1H); 7.07 (d, 2H); 6.94 (d, 1H); 6.87 (d, 2H); 5.18 (s, 2H); 4.32 (s, 2H); 2.47 (t, 2H); 1.46 (quint., 2H); 1.23 (sext., 2H); 0.78 (t, 3H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in water
  5. filtrationThe precipitated solid was recovered by filtration
  6. customrecrystallized from acetone

Sources & evidence

ORD record
ord-586a38fbb84c4f4f8f0ab0fa1bfc589f
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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