Hydrochloric Acid → 4-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoic acid

HRID 583653Notes

Reaction equation

HRID 583653 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=2)[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18928610Methyl 4-[2-(1-Benzylimidazol-4-yl)ethyloxy]benzoate

Product 1

HCID 158507574-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-5 (170 mg, 0.51 mmol), 1N NaOH (5 mL), and CH3OH (10 mL) was stirred at ambient temperature for 20 h. The reaction mixture was cooled to 0° C., neutralized with 1N HCl (5 mL), and then concentrated. The solid was extracted with CHCl3 and the combined extracts concentrated to give 3-6 as a gelatinous solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. concentrationconcentrated
  3. extractionThe solid was extracted with CHCl3
  4. concentrationthe combined extracts concentrated

Sources & evidence

ORD record
ord-8a6135e68bf04239aa7cc70c3c5682e9
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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