Ethyl Acetate → HCID 19811356, compound

HRID 2291966Notes

Reaction equation

HRID 2291966 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16].C(OCC)(=O)C>CS(C)=O>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH:16][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 66053N,N-DimethylethylenediamineHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 19811356HCID 19811356, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of 2,4-difluoronitrobenzene (3.18 g., 20 mmole) In DMSO (5 ml) was added portion-wise N,N-dimethylethylene-diamine (3.52 g., 40 mmole). The mixture was stirred at 23° C. for 1 hour and poured into crushed ice. Ethyl acetate (200 ml) was added to dissolve the orange-yellow solid. The organic phase separated was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed on a silica gel column eluting with CH2Cl2 /MeOH (20:1) to afford the compound (15) (2.8 g., 62%) which solidified on standing.

Workup

  1. additionpoured
  2. custominto crushed ice
  3. dissolutionto dissolve the orange-yellow solid
  4. customThe organic phase separated
  5. washwas washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was chromatographed on a silica gel column
  9. washeluting with CH2Cl2 /MeOH (20:1)

Sources & evidence

ORD record
ord-e41d1517a90d406182ab963f867ac2d8
Source dataset
uspto-grants-1989_01
Patent number
US04799934

Reaction notes

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