Sodium hydride → Benzaldehyde, 4-(4-methyl-1H-imidazol-1-yl)-

HRID 1645831Notes

Reaction equation

HRID 1645831 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.F[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1>CN(C)C=O>[CH3:3][C:4]1[N:5]=[CH:6][N:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 178418800HCID 178418800, compound

Product 1

HCID 15045260Benzaldehyde, 4-(4-methyl-1H-imidazol-1-yl)-Yield 14.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.20 g of sodium hydride (a 60% suspension thereof in a mineral oil) was suspended in 150 ml of dimethylformamide to obtain a suspension. 8.62 g of 4-methylimidazol was added to the suspension at a room temperature under stirring in portions. After one hour, 12.4 g of 4-fluorobenzaldehyde was added to the obtained mixture. The obtained mixture was stirred for 4 hours and poured into ice-water. The obtained mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and distilled under a reduced pressure to remove the solvent. The obtained residue was purified by silica gel column chromatography (solvent: chloroform/methanol (50:1)) to obtain a solid product. This solid product was washed with ether to obtain 2.67 g of the title compound as a pale yellow powder (yield: 14%).

Workup

  1. customto obtain a suspension
  2. stirringThe obtained mixture was stirred for 4 hours
  3. extractionThe obtained mixture was extracted with chloroform
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationdistilled under a reduced pressure
  6. customto remove the solvent
  7. customThe obtained residue was purified by silica gel column chromatography (solvent: chloroform/methanol (50:1))
  8. customto obtain a solid product
  9. washThis solid product was washed with ether

Sources & evidence

ORD record
ord-d17ac81fdcda488fb42458409431de1c
Source dataset
uspto-grants-1993_01
Patent number
US05177089

Reaction notes

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