Methanol → HCID 178418785, compound

HRID 1409422Notes

Reaction equation

HRID 1409422 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]1.OS(O)(=O)=O.[CH3:14]O>>[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:14])=[O:7])[N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178524800HCID 178524800, compound

Product 1

HCID 178418785HCID 178418785, compound

Conditions

Temperature
80 °C

Procedure

1H-Imidazole-4-carboxylic acid (5 g, 44.6 mmol) was dissolved in MeOH (100 ml). Into the solution, H2SO4 (10 ml) was added at 0° C. The resulting mixture was stirred at 80° C. for overnight. The solvent was concentrated under reduced pressure. The pH was adjusted to 9 with aqueous NaHCO3 solution and extracted with EtOAc. The organic layer was concentrated to give the product. Yield 5.2 g. 1H-NMR (400 MHz; DMSO-d6): δ 3.74 (s, 3H), 7.79 (bs, 2H), 12.75 (bs, 1H). LC-MS: [M+1]=127.23.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. customto give the product

Sources & evidence

ORD record
ord-2105f93dde3441d292b7d39b9db5b053
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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