HCID 19815285, compound → HCID 19815439, compound

HRID 465789Notes

Reaction equation

HRID 465789 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[C:22]([CH2:23][OH:24])=[C:21]([Cl:25])[N:20]=[C:19]3[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([O:3]C)=[O:2]>C(O)C.[OH-].[Na+]>[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[C:22]([CH2:23][OH:24])=[C:21]([Cl:25])[N:20]=[C:19]3[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 19815285HCID 19815285, compound

Product 1

HCID 19815439HCID 19815439, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.30 g of 1-[(3'-carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole in 16 mL of ethanol and 8 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 aqueous ethanol to furnish 0.24 g of 1-[(3'-carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole (m.p. 180°-181°); NMR (200 MHz, DMSO-d6): δ8.26 (s, 1H); 8.04 (d, 1H); 7.77 (d, 1H); 7.52 (t, 1H); 7.36 (A2M2, 4H); 5.30 (s, 2H); 4.48 (s, 2H); 2.57 (t, 2H); 1.64 (quint., 2 H); 1.34 (sext., 2H); 0.87 (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 aqueous ethanol

Sources & evidence

ORD record
ord-a7ed7f4ab2cb409f8f9056d8a04bdcf5
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Reaction notes

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