Sulfuric Acid → Imidazole-4-acetic acid

HRID 1987384Notes

Reaction equation

HRID 1987384 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:4]=[CH:3]1.S(=O)(=O)(O)O>CO>[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178479752HCID 178479752, compound

Product 1

HCID 96215Imidazole-4-acetic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-imidazoleacetic acid hydrochloride (499 mg, 3.07 mmol) in MeOH (10 mL) was added concentrated sulfuric acid (1 mL) and the mixture was heated to 80° C. overnight. Then the mixture was cooled and concentrated. The residue was dissolved in CH2Cl2 (30 mL) and washed with saturated NaHCO3 (30 mL). The aqueous layer was saturated with NaCl (s) and extracted with EtOAc (3×30 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to afford (1H-imidazol-4-yl)-acetic acid mnethyl ester as a yellow oil (330 mg, 66%). 1H NMR (CDCl3) δ 3.70 (s, 2H), 3.72 (s, 3H), 6.97 (s, 1H), 7.59 (s, 1H).

Workup

  1. temperatureThen the mixture was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2 (30 mL)
  4. washwashed with saturated NaHCO3 (30 mL)
  5. extractionextracted with EtOAc (3×30 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3704a33ad0124617b4e602c8efd3976c
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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