Methanol → HCID 9866601, compound

HRID 1085817Notes

Reaction equation

HRID 1085817 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S: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.O.[OH-].[Li+].CO>O>[C:12]1([C:11]2[N:10]=[C:9]([S: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:8][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 54116126HCID 54116126, compound

Product 1

HCID 9866601HCID 9866601, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl [3-[[(4,5-diphenyl-1H-imidazol-2-yl)thio]methyl]phenoxy]acetate (2.00 g, 4.6 mmol), lithium hydroxide monohydrate (586 mg, 14 mmol), methanol (35 mL) and water (10 mL) was stirred at room temperature for 2 hours. The solvent was evaporated, the residue diluted with water and 2N HCl solution added to pH=7. A white solid was filtered off and recrystallized from aqueous DMF to give [3-[[(4,5-diphenyl-1H-imidazol-2-yl)thio]methyl]phenoxy]acetic acid (1.33 g, 69%), m.p. 233°-235° C.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water and 2N HCl solution
  3. additionadded to pH=7
  4. filtrationA white solid was filtered off
  5. customrecrystallized from aqueous DMF

Sources & evidence

ORD record
ord-5fff16d28edb404395c487c8cf6266fb
Source dataset
uspto-grants-1991_04
Patent number
US05011851

Reaction notes

Loading…