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

HRID 1368634Notes

Reaction equation

HRID 1368634 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:4]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:3]1.[C:25]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26].[OH-:39].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:25]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([N:7]([S:35]([C:32]2[CH:33]=[CH:34][C:29]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:30][CH:31]=2)(=[O:36])=[O:39])[C:6]2[N:2]([CH3:1])[N:3]=[C:4]([O:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]=2[C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 222820241-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-amine

Product 1

HCID 222819394-(tert-butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl)-N-[1-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-yl]benzenesulfonamideYield 43.5%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 1-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-amine (Preparation 2) (105 mg) in dichloromethane (5 ml) at room temperature was added 4-tert-butylbenzenesulfonylchloride (265 mg), tetrabutylammonium hydrogen sulfate (28 mg) and potassium hydroxide (265 mg). The mixture was sonicated for 3 hrs. The reaction was diluted with water (10 ml) and extracted with ethyl acetate (10 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography silica (10 g) eluted with dichloromethane to yield the title compound as a white solid (101 mg).

Workup

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

Sources & evidence

ORD record
ord-34c485bb7f8d411d973091b4bef0cfd3
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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