4-Nitrophenol → HCID 14622571, compound

HRID 1638711Notes

Reaction equation

HRID 1638711 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]([CH3:19])[S:6]([C:9]1[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)(=[O:8])=[O:7].[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)([O-:23])=[O:22].[H-].[Na+]>CN(C)C=O>[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]([CH3:19])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:30][C:27]2[CH:28]=[CH:29][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=2)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 14622557HCID 14622557, compound

Product 1

HCID 14622571HCID 14622571, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2- dimethylaminoethyl)-N-methyl-4- chloro-3-nitrobenzenesulfonamide (2.2 g, 6.84 mmol) and 4- nitrophenol (0.97 g, 7.0 mmol) in dimethylformamide (30 mL) was added 60% sodium hydride-mineral oil suspension (0.28 g, 7.0 mmol). The resulting solution was stirred at 60° for 20 hours under N2. After concentrating under reduced pressure at 50° , the residue was partitioned between ethyl acetate and water. The ethyl acetate extract was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was flash chromatographed over silica gel and 2.8 g of the nitrophenyl ether eluted with 3% methanol-97% chloroform.

Workup

  1. concentrationAfter concentrating under reduced pressure at 50°
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed over silica gel and 2.8 g of the nitrophenyl ether
  9. washeluted with 3% methanol-97% chloroform

Sources & evidence

ORD record
ord-007b5f44fa5c4430b834d72fdb17f2ac
Source dataset
uspto-grants-1989_11
Patent number
US04880821

Reaction notes

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