Hydrochloric Acid → Imidazole-1-acetic acid

HRID 1279730Notes

Reaction equation

HRID 1279730 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][C:10]([OH:12])=[O:11].Cl>C1COCC1.O>[N:1]1([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 6227Bromoacetic AcidHCID 24758Sodium hydride

Product 1

HCID 656129Imidazole-1-acetic acidYield 31.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Imidazole (3.7 g, 54 mmol) was added to a suspension of sodium hydride (2.6 g of a 60% dispersion in oil, 60 mmol) in 50 ml dry THF. Bromoacetic acid (3.4 g, 24 mmol) was then added and the mixture stirred overnight. Water (1 ml) was then added and the solvent removed under reduced pressure. The residue was taken up in water (50 ml, pH>10), extracted with ether and the organic layer discarded. The aqueous layer was acidified to pH 1 with concentrated HCl and extracted again with ether. The aqueous layer was evaporated to dryness. The oily residue was dissolved in absolute ethanol (EtOH) to precipitate NaCl, and recrystallized from acetone/methanol to give 1.22 g (7.5 mmol, 30%) pure product as the hydrochloride. 1H NMR: (DMSO-d6, 200 MHz) δ 9.20 (s, H2), 7.76 (d, J=1.5 Hz), 7.69 (d, J=1.5 Hz), 5.20 (s, CH2).

Workup

  1. customthe solvent removed under reduced pressure
  2. extractionextracted with ether
  3. extractionextracted again with ether
  4. customThe aqueous layer was evaporated to dryness
  5. dissolutionThe oily residue was dissolved in absolute ethanol (EtOH)
  6. customto precipitate NaCl
  7. customrecrystallized from acetone/methanol

Sources & evidence

ORD record
ord-08bb6e6ce853415fa3cbbc15452cbeef
Source dataset
uspto-grants-2002_09
Patent number
US06448373B1

Reaction notes

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