Ethyl Acetate → HCID 19811390, compound

HRID 373070Notes

Reaction equation

HRID 373070 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1[N+:16]([O-])=O.[H][H].[C:22](OCC)(=[O:24])C>[Pd]>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:6]2[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=2[NH:16][C:22]1=[O:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 19811314HCID 19811314, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19811390HCID 19811390, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In ethyl acetate (20 ml) was dissolved N,N-dimethyl-N'-(2-nitro-5-trifluoromethylphenyl)ethylenediamine (0.24 g) followed by addition of a catalytic amount of 10% palladium-on-carbon, and the mixture was stirred under a hydrogen atmosphere at atmospheric pressure and room temperature until the absorption of hydrogen was ceased (for about 1 hour). The insoluble matter was filtered off and the solvent was distilled off under reduced pressure. The residue was dissolved in N,N-dimethylformamide (2 ml) followed by addition of N,N'-disuccinimidyl carbonate (DSC) (0.23 g). The reaction mixture was stirred at room temperature overnight, after which it was diluted with 1N hydrochloric acid and washed with ethyl acetate. The aqueous layer was alkalized with sodium hydroxide and the product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by column chromatography (eluent:chloroform:methanol=5:1) to give 0.11 g of 1,3-dihydro-1-(2-dimethylaminoethyl)-6-trifluoromethyl-2H-benzimidazol-2-one.

Workup

  1. custom(for about 1 hour)
  2. filtrationThe insoluble matter was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in N,N-dimethylformamide (2 ml)
  5. additionfollowed by addition of N,N'-disuccinimidyl carbonate (DSC) (0.23 g)
  6. additionafter which it was diluted with 1N hydrochloric acid
  7. washwashed with ethyl acetate
  8. extractionthe product was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was then distilled off under reduced pressure
  12. customthe residue was purified by column chromatography (eluent:chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-ec566c6ac255462f95ffaea838f4c6f5
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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