Sodium Carbonate → HCID 14450253, compound

HRID 1681387Notes

Reaction equation

HRID 1681387 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH3:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH3:12][C:13]1[N:14]=[CH:15][N:16]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 178418800HCID 178418800, compound

Product 1

HCID 14450253HCID 14450253, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-fluoro-2nitrotoluene (1.05 g), 4-methylimidazole (556 mg) and sodium carbonate (753 mg) in dimethylformaldehyde (23 ml) was heated under stirring for 36 hours. The reaction mixture was distilled under reduced pressure to remove solvent. The residue was dissolved in water and the solution was acidified with 4N HCl solution to pH 5 and extracted with chloroform. The water layer was made to pH 10 with 2.5N sodium hydroxide solution, extracted with chloroform, dried with MgSO4 and filtered. The solution was distilled to give 1.09 g (74%) of the title compound.

Workup

  1. temperaturewas heated
  2. distillationThe reaction mixture was distilled under reduced pressure
  3. customto remove solvent
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with chloroform
  6. extractionextracted with chloroform
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. distillationThe solution was distilled

Sources & evidence

ORD record
ord-eb744777aacc47f48a2b5e4e39d3dc63
Source dataset
uspto-grants-1992_12
Patent number
US05171851

Reaction notes

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