Sodium Hydroxide → HCID 23664226, compound

HRID 1167346Notes

Reaction equation

HRID 1167346 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[NH:14][CH:15]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:17]=1)C.[OH-].[Na+:34]>O1CCOCC1>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:15]2[CH:16]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[NH:17][C:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][CH2:5][C:4]([O-:32])=[O:3])=[N:14]2)=[CH:30][CH:29]=1.[Na+:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69148411HCID 69148411, compound

Product 1

HCID 23664226HCID 23664226, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

{2-[4,5-Bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-phenoxy)-acetic acid ethyl ester (35 mg, 0.075 mmol) was dissolved in 1.5 mL of dioxane, and 0.5 M sodium hydroxide solution (1.5 mL, 0.75 mmol) was added. The reaction mixture was stirred at room temperature for 23 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (Biotage system, 12S-C18 reverse phase) eluting with 0-25% acetonitrile in water to afford sodium {2-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-phenoxy}-acetate (22 mg, 63%). HR-MS (ES, m/z) calculated for C23H19N2O3Cl2 [(M−Na+2H)+] 441.0767, observed 441.0767.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (Biotage system, 12S-C18 reverse phase)
  3. washeluting with 0-25% acetonitrile in water

Sources & evidence

ORD record
ord-ce94c4de8d4a4c87bb2bebf5033fcf95
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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