4-tert-Butylphenol → HCID 20097726, compound

HRID 1769818Notes

Reaction equation

HRID 1769818 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[H][H].F[C:17]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>CN(C)C=O.O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([O:13][C:17]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][C:18]=2[C:19]([NH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:20])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 9859981N-Phenyl-2-fluoro-5-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 20097726HCID 20097726, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 0.18 g (6 mmole) of 80% sodium hydride in 7.5 ml of dry dimethylformamide was slowly added 0.9 g (6 mmole) of 4-t-butylphenol in 2.5 ml of dimethylformamide. After cessation of hydrogen evolution, 1.3 g (5 mmole) of solid 2-fluoro-5-nitrobenzanilide was added and the deep red solution was stirred at room temperature for 5 days. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with IN hydrochloric acid, saturated aqueous sodium bicarbonate solution, dried with magnesium sulphate and the solvent removed to yield the crude product. Recrystallisation from methylene chloride and hexare yielded 0.92 g product (47%) m.p. 138°-140° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with IN hydrochloric acid, saturated aqueous sodium bicarbonate solution
  3. dry with materialdried with magnesium sulphate
  4. customthe solvent removed
  5. customto yield the crude product
  6. customRecrystallisation from methylene chloride and hexare

Sources & evidence

ORD record
ord-a99d0930f4244c39b8beddca70842091
Source dataset
uspto-grants-1995_01
Patent number
US05382682

Reaction notes

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