Sodium Hydroxide → 5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentanoic acid

HRID 1033247Notes

Reaction equation

HRID 1033247 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 10094797ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate

Product 1

HCID 100473085-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentanoic acid

Procedure

Part B. The ester prepared in Part A above (14.4 g, 32.6 mmol) was stirred in ethanolic sodium hydroxide (240 mL, 0.25N, 60 mmol, about 5% water added) at ambient temperature for 48 hours. The reaction mixture was evaporated, neutralized to pH 7 with small portions of 1N aqueous hydrochloric acid, and saturated with sodium chloride. This mixture was extracted with ethyl acetate (2×200 mL), and the extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoic acid as a waxy solid (12.1 g, 29.3 mmol, 90%).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionThis mixture was extracted with ethyl acetate (2×200 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8bb5f135edc340f295a288e028b1d48d
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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