Sodium Hydroxide → 4-(tert-butyl)-N-[1-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-yl]benzenesulfonamide

HRID 1368573Notes

Reaction equation

HRID 1368573 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14](S(C2C=CC(C(C)(C)C)=CC=2)(=O)=O)[C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:16]=2[C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:16]=2[C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 222819394-(tert-butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl)-N-[1-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-yl]benzenesulfonamide

Product 1

HCID 222819144-(tert-butyl)-N-[1-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-yl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 4-(tert-butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl}-N-[1-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-yl]benzenesulfonamide (Preparation 1) (80 mg) in ethanol (20 ml) at room temperature was added sodium hydroxide (2N, 2 ml) and the mixture was stirred for 16 hrs. The mixture was reduced in volume to 10 ml under reduced pressure, diluted with water (50 ml) and extracted with ethyl acetate (30 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10 g) eluted with dichloromethane:ether (7:1) to yield the title compound as a colourless glass-like solid (7 mg).

Workup

  1. extractionextracted with ethyl acetate (30 ml)
  2. dry with materialThe organic fraction was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica (10 g)
  6. washeluted with dichloromethane:ether (7:1)

Sources & evidence

ORD record
ord-b250d0bde93644cca0b9b681e4b8965a
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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