Methanol → HCID 178418812, compound

HRID 1784215Notes

Reaction equation

HRID 1784215 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.[CH3:16]O>>[CH3:16][O:9][C:8](=[O:10])[CH2:7][C:5]1[N:4]=[CH:3][NH:2][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178479752HCID 178479752, compound

Product 1

HCID 178418812HCID 178418812, compoundYield 66%

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 methyl 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-b6e38debdb4e4f89bdadcddf63a58b91
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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