4-Nitrophenol → HCID 53757149, compound

HRID 1638713Notes

Reaction equation

HRID 1638713 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][N:9]([CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+]([O-])=O)[CH:14]=1)(=[O:12])=[O:11].[CH:31]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[C:33]([OH:40])[CH:32]=1.[H-].[Na+]>CN(C)C=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][N:9]([CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([O:40][C:33]2[CH:32]=[CH:31][C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=2)[CH:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 19841414HCID 19841414, compound

Product 1

HCID 53757149HCID 53757149, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the chloro derivative from Step 2 (6.5 g, 13.2 mmol) and p-nitrophenol (1.95 g, 14.0 mmol) in dimethylformamide (75 mL) was added 60% sodium hydride mineral oil suspension (0.56 g, 14.0 mmol). The resulting solution was stirred at 60° under nitrogen for 19 hours. After concentrating under reduced pressure at 60° , the residue was partitioned between ethyl acetate and brine. The organic extract was dried (Na2SO4) filtered and concentrated. The residue was flash chromatographed over silica gel and 6.8 g of pure product was eluted with 15% ethyl acetate - 85% n-butylchloride.

Workup

  1. concentrationAfter concentrating under reduced pressure at 60°
  2. customthe residue was partitioned between ethyl acetate and brine
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed over silica gel and 6.8 g of pure product
  8. washwas eluted with 15% ethyl acetate - 85% n-butylchloride

Sources & evidence

ORD record
ord-71e974432c1a4ba98a75d8d22c58c5eb
Source dataset
uspto-grants-1989_11
Patent number
US04880821

Reaction notes

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