Acetaminophen → HCID 68460957, compound

HRID 2197944Notes

Reaction equation

HRID 2197944 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].C1COCC1.[F:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[C:26](F)[CH:25]=1>CS(C)=O.O>[F:23][C:24]1[CH:25]=[C:26]([CH:27]=[C:28]([N+:30]([O-:32])=[O:31])[CH:29]=1)[O:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1983AcetaminophenHCID 752721,3-Difluoro-5-nitrobenzeneHCID 66863523KOtBu THF

Product 1

HCID 68460957HCID 68460957, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of N-(4-hydroxyphenyl)acetamide (1.00 g, 6.5 mmol) in DMSO (12 ml) was added 1M t-BuOK/THF solution (7.13 ml, 7.13 mmol) dropwise at room temperature and the mixture was stirred at room temperature for 30 minutes under N2 flow. 1,3-Difluoro-5-nitrobenzene (0.89 ml, 7.8 mmol) was added at room temperature, and then the mixture was stirred at room temperature for 2 hours and at 50° C. for 2 hours under a N2 flow. 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 title compound as a pale brown solid, which was purified by washing with i-Pr2O to give the desired product as slightly brown crystal (1.73 g, 92%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours and at 50° C. for 2 hours under a N2 flow
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with EtOAc
  4. washThe extract washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ccfdf054395549fcacb6876c86419968
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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