2,4-Dimethoxybenzaldehyde → 1-Hydroxy-2-(2,4-dimethoxyphenyl)-5-methyl-4-(4-pyridyl)imidazole

HRID 620818Notes

Reaction equation

HRID 620818 reaction equation
[OH:1][N:2]=[C:3]([CH3:12])[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.O.[NH3:14].[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH:19]=O>O1CCOCC1.C(O)C>[OH:1][N:2]1[C:3]([CH3:12])=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[N:14]=[C:19]1[C:18]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:17]=1[O:16][CH3:15]

Participants

6

Reactant 3

HCID 691752,4-DimethoxybenzaldehydeHCID 12896473Azane;hydrateHCID 587523384-(2-Hydroxyiminopropionyl)pyridine

Product 1

HCID 212452841-Hydroxy-2-(2,4-dimethoxyphenyl)-5-methyl-4-(4-pyridyl)imidazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 4-(2-hydroxyiminopropionyl)pyridine (2.0 g) in a mixture of dioxane (40 ml) and ethanol were added conc. ammonia water (58 ml) and 2,4-dimethoxybenzaldehyde (2.02 g), and the mixture was stirred at ambient temperature for 1 week. After evaporation, the mixture was triturated with chloroform to give 1-hydroxy-2-(2,4-dimethoxyphenyl)-5-methyl-4-(4-pyridyl)imidazole (3.01 g).

Workup

  1. customAfter evaporation
  2. customthe mixture was triturated with chloroform

Sources & evidence

ORD record
ord-4880206bad6248c0892eec9daa45948d
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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