Sodium Hydroxide → HCID 20059011, compound

HRID 1085814Notes

Reaction equation

HRID 1085814 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([O:27]C)=[O:26])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([OH:27])=[O:26])[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10319484HCID 10319484, compound

Product 1

HCID 20059011HCID 20059011, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [3-(2-(4,5-diphenyl-1H-imidazol-2-yl)ethyl]phenoxy]acetate (l.20 g, 3 mmol), 5N NaOH solution (l.74 mL, 9 mmol) and methanol (30 mL) was heated to reflux on a steam bath for 20 minutes. The solvent was removed, the residue diluted with water and acidified to pH=1 with 2N HCl solution. A yellow solid was filtered off and subjected to chromatography on a column of silica gel using a mixture of chloroform and methanol (9:1) as eluent to give [3-[2-(4,5-diphenyl-1H-imidazol-2-yl)ethyl]phenoxy]-acetic acid (0.42 g, 36%), mp 244°-246° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux on a steam bath for 20 minutes
  3. customThe solvent was removed
  4. additionthe residue diluted with water
  5. filtrationA yellow solid was filtered off
  6. additiona mixture of chloroform and methanol (9:1) as eluent

Sources & evidence

ORD record
ord-f79b56f3cb2f490c8b574d8f7b4a7687
Source dataset
uspto-grants-1991_04
Patent number
US05011851

Reaction notes

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