Sodium Hydroxide → HCID 18399504, compound

HRID 1019042Notes

Reaction equation

HRID 1019042 reaction equation
[N:1]1([CH2:6]/[CH:7]=[CH:8]/[C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>CO>[N:1]1([CH2:6]/[CH:7]=[CH:8]/[C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18399500HCID 18399500, compound

Product 1

HCID 18399504HCID 18399504, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(2,4-difluorophenyl)benzoate (0.9 g; 2.54 mmol) and 2N sodium hydroxide solution (3.8 ml) in methanol was heated at reflux for 7 hours. After evaporation of the solvent and neutralisation to pH 6.5 with 6N HCl, the residue was purified on reverse phase silica eluting with methanol/ammonium carbonate buffer (2 g/l, pH 7) (50/50) to give 4-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(2,4-difluorophenyl)benzoic acid after freeze-drying. Yield: 49%.

Workup

  1. temperatureat reflux for 7 hours
  2. customAfter evaporation of the solvent and neutralisation to pH 6.5 with 6N HCl
  3. customthe residue was purified on reverse phase silica eluting with methanol/ammonium carbonate buffer (2 g/l, pH 7) (50/50)

Sources & evidence

ORD record
ord-a0dfe73463aa4f7ea8386f804d630032
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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