Water → HCID 14211365, compound

HRID 620829Notes

Reaction equation

HRID 620829 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[NH:12][C:13]([CH3:22])=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:15]=1.[H-].[Na+].[CH3:25]I.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:12]([CH3:25])[C:13]([CH3:22])=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10017395HCID 10017395, compound

Product 1

HCID 14211365HCID 14211365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2,4-dimethoxyphenyl)-5-methyl-4-(3-pyridyl)imidazole (0.80 g) in N,N-dimethylformamide (12 ml) was added sodium hydride (0.13 g, 60% suspension in oil), and the mixture was stirred for 10 minutes. Then methyl iodide (0.34 ml) was added thereto, and the reaction was stirred at ambient temperature for 5 hours. The solution was poured into water (100 ml), and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, and chromatographed on silica gel (25 g) eluting with chloroform. The fractions were collected and evaporated, and the residue was triturated with a mixture of ethyl acetate and diisopropyl ether (1:1 V/V) to give 2-(2,4-dimethoxyphenyl)-1,5-dimethyl-4-(3-pyridyl)imidazole (70 mg).

Workup

  1. stirringthe reaction was stirred at ambient temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. customchromatographed on silica gel (25 g)
  6. washeluting with chloroform
  7. customThe fractions were collected
  8. customevaporated
  9. customthe residue was triturated with a mixture of ethyl acetate and diisopropyl ether (1:1 V/V)

Sources & evidence

ORD record
ord-e2a89bdd94674887aec86be2390157fa
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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