Sodium hydride → HCID 19926616, compound

HRID 373932Notes

Reaction equation

HRID 373932 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[N+:10]([C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)([O-:12])=[O:11].[H-].[Na+]>CN(C)C=O>[N+:10]([C:13]1[N:14]=[CH:15][N:16]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:17]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 178526856HCID 178526856, compound

Product 1

HCID 19926616HCID 19926616, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 18.6 g of 4-fluorobenzaldehyde and 18.6 g of 4-nitroimidazole in 70 ml of dimethylformamide was dropwise added to a suspension of 6.6 g of sodium hydride (60% suspension in mineral oil) in 150 ml of dimethylformamide at a room temperature under stirring. The obtained mixture was stirred at 90° C. for about 5 hours, cooled and poured into ice-water to precipitate a solid. This solid was recovered by filtration, washed with water and heated together with ethanol. The mixture was cooled and filtered. The obtained solid was washed with ethanol to obtain 18 g of the title compound as a white powder (yield: 55%).

Workup

  1. stirringThe obtained mixture was stirred at 90° C. for about 5 hours
  2. temperaturecooled
  3. customto precipitate a solid
  4. filtrationThis solid was recovered by filtration
  5. washwashed with water
  6. temperatureheated together with ethanol
  7. temperatureThe mixture was cooled
  8. filtrationfiltered
  9. washThe obtained solid was washed with ethanol

Sources & evidence

ORD record
ord-80439b78bb134d2a8b555f2ca0c87517
Source dataset
uspto-grants-1992_11
Patent number
US05166188

Reaction notes

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