Ethyl Acetate → N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide

HRID 491634

Reaction equation

HRID 491634 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](F)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[C:14]([NH:17][C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)(=[O:16])[CH3:15].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:24][C:20]1[CH:19]=[C:18]([NH:17][C:14](=[O:16])[CH3:15])[CH:23]=[CH:22][CH:21]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 121243-HydroxyacetanilideHCID 2986753,4-Dinitrofluorobenzene

Product 1

HCID 86002098N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 3,4-dinitrofluorobenzene (1.0 g, 5.4 mmol, 1.0 eq.) and 3-acetamidophenol (0.8 g, 5.4 mmol, 1.0 eq.) in 10 mL of anhydrous DMF, K2CO3 (0.7 g, 5.4 mmol, 1.0 eq) was added. The reaction mixture was heated to 120° C. and stirred for 16 h. The mixture was cooled to RT and EtOAc was added (100 mL). After washing with H2O (100 mL), the organic layer was dried (MgSO4), filtered and concentrated. The resulting crude material was purified by column chromatography (20-100% EtOAc in hexanes) to obtain pure N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled to RT
  3. washAfter washing with H2O (100 mL)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude material was purified by column chromatography (20-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-207a6e02ee8e4ede907d6463bba283b7
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Linked notes

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