Methanol → HCID 178418812, compound

HRID 901119Notes

Reaction equation

HRID 901119 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([OH:9])=[O:8])[N:3]=[CH:2]1.[Na].[CH3:11]O>>[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([O:9][CH3:11])=[O:8])[N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 96215Imidazole-4-acetic acidHCID 5360545Sodium

Product 1

HCID 178418812HCID 178418812, compound

Procedure

A solution of 4-Imidazoleacetic acid, sodium salt, hydrate (compound ix, where R2 is H) (3.0 g, 18.1 mmol) in MeOH (50 ml) was cooled to about 0° C. and anhydrous HCl gas was bubbled into the mixture for about 15 minutes while maintaining reaction temperature below about 5° C. The reaction was stirred for about 12 hour at room temperature and then solvents were removed under reduced pressure to yield an oil which solidifies on standing. Mass spec 141.0 MH+, NMR (300 MHZ, DMSO-d6, 30° C.), 9.0-9.2 (1H, s), 7.47.6 (1H, s), 3.85-3.95 (2H, 3), 3.6-3.7 (3H, s).

Workup

  1. customanhydrous HCl gas was bubbled into the mixture for about 15 minutes
  2. temperaturewhile maintaining
  3. customreaction temperature below about 5° C
  4. customsolvents were removed under reduced pressure
  5. customto yield an oil which

Sources & evidence

ORD record
ord-cdddd3d1ac58482cb26e430519f913f9
Source dataset
uspto-grants-2008_04
Patent number
US07361656B2

Reaction notes

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