Sodium hydride → HCID 23079305, compound

HRID 1173945Notes

Reaction equation

HRID 1173945 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].I[CH2:9][CH2:10][O:11][CH2:12][O:13][CH3:14].[H-].[Na+]>CN(C=O)C>[CH3:14][O:13][CH2:12][O:11][CH2:10][CH2:9][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 249551H-imidazole-2-carbaldehydeHCID 11117431HCID 11117431, compound

Product 1

HCID 23079305HCID 23079305, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (15 ml), 2-imidazole carboxaldehyde (300 mg) was dissolved. Then, the compound (1.01 g) obtained in Example 92-1 and sodium hydride (137 mg) were added to the solution, and the whole was stirred at room temperature for 5 days. After completion of the reaction, the solvent was distilled off and the residue was then added with chloroform, followed by washing with water and saturated saline solution. The resultant was dried with anhydrous sodium sulfate, and the solvent was distilled off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (457 mg) as a yellow viscous liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was then added with chloroform
  4. washby washing with water and saturated saline solution
  5. dry with materialThe resultant was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-9e1f411ae7584742ab3dc5b24c6b567d
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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