Ethanol → HCID 13228938, compound

HRID 1380548Notes

Reaction equation

HRID 1380548 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[CH:12]=2)[C:6]=1CC#N.[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28]>>[Cl:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[CH:12]=2)[C:6]=1[CH2:28][C:27]([OH:25])=[O:29]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13228944HCID 13228944, compound

Product 1

HCID 13228938HCID 13228938, compound

Procedure

4-Chloro-5-cyanomethyl-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole (1 g) was dissolved in 10 ml of ethanol, and 10 ml of 2 N-sodium hydroxide was added. The mixture was boiled for 4 hours and evaporated to dryness, and the residue was shaken with 20 ml each of chloroform and water. The aqueous layer was washed with chloroform and 10 ml of 2N-hydrochloric acid was added. The resulting syrupy precipitate was recrystallized from aqueous ethanol to give 0.5 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless needles, m.p. 192°-195° C. (decompn.).

Workup

  1. customevaporated to dryness
  2. washThe aqueous layer was washed with chloroform and 10 ml of 2N-hydrochloric acid
  3. additionwas added
  4. customThe resulting syrupy precipitate was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-ead52b67bd2141789b45736d3668ea93
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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