Acetaminophen → N-[4-(3-Chloro-5-nitro-phenoxy)-phenyl]-acetamide

HRID 2197947Notes

Reaction equation

HRID 2197947 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 330981-Chloro-3,5-dinitrobenzene

Product 1

HCID 68460873N-[4-(3-Chloro-5-nitro-phenoxy)-phenyl]-acetamideYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 193a (1.06 g, 5.2 mmol), N-(4-hydroxyphenyl)acetamide (0.70 g, 4.5 mmol) and K2CO3 (0.79 g, 5.7 mmol) in DMF (14 ml) was heated at 110° C. for 6 hours. The reaction mixture was cooled to room temperature, diluted with H2O and then extracted with EtOAc. The extract washed with H2O and brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound as a pale brown crystal, which was purified by washing with i-Pr2O to give the desired product as pale brown crystal (1.28 g, 92%).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound as a pale brown crystal, which
  7. customwas purified
  8. washby washing with i-Pr2O

Sources & evidence

ORD record
ord-03c3545eada8456babb1c4b4d50bfdc6
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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