Acetaminophen → HCID 9110895, compound

HRID 2197891Notes

Reaction equation

HRID 2197891 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:22][C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:12](=[O:14])[CH3:13])=[CH:21][CH:20]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 3

HCID 1983AcetaminophenHCID 10796Cesium carbonateHCID 676604-Chloro-1-fluoro-2-nitrobenzene

Product 1

HCID 9110895HCID 9110895, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-Fluoro-5-Chloro Nitro benzene (0.5 g, 2.85 mmol), 4-Acetamidophenol (0.45 g, 3.00 mmol) and cesium carbonate (0.98 g, 3.00 mmol) in DMSO (5 mL) was heated 6 hr at 90° C. The mixture was cooled, diluted with ethyl acetate (100 mL) and the organic layer washed with water, 20% aqueous potassium hydroxide solution and aqueous 10% sodium chloride solution, then dried over anhydrous sodium sulfate. The drying agent was filtered and the solvent concentrated under vacuum leaving the title compound as a tan solid (0.71 g, 81%).

Workup

  1. temperatureThe mixture was cooled
  2. washthe organic layer washed with water, 20% aqueous potassium hydroxide solution and aqueous 10% sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. concentrationthe solvent concentrated under vacuum

Sources & evidence

ORD record
ord-e0762df9665942e9b86aa6abff517458
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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