Acetic Acid → Methyl 5-formyl-1H-imidazole-4-carboxylate

HRID 1971069Notes

Reaction equation

HRID 1971069 reaction equation
[CH2:1]([O:3][CH:4]([O:14]CC)[C:5]1[N:6]=[CH:7][NH:8][C:9]=1[C:10](OC)=[O:11])C.C(O)(=O)C>O>[CH:10]([C:9]1[N:8]=[CH:7][NH:6][C:5]=1[C:4]([O:3][CH3:1])=[O:14])=[O:11]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178471178HCID 178471178, compound

Product 1

HCID 178499152Methyl 5-formyl-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of Intermediate 1B (5.65 g, 24.75 mmol) in water (12 mL) was added acetic acid (49 mL, 0.86 mol). The resulting mixture was stirred under nitrogen for 6 hours. The reaction mixture was azeotroped with toluene and dried under vacuum to give the desired aldehyde, Intermediate 1C in quantitative yield as a white solid, which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was azeotroped with toluene
  2. customdried under vacuum

Sources & evidence

ORD record
ord-6db8fdf0aa2e4b39a7a77db972daaa94
Source dataset
uspto-grants-2013_04
Patent number
US08431565B2

Reaction notes

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