Sodium Hydroxide → HCID 22281957, compound

HRID 397279Notes

Reaction equation

HRID 397279 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][CH3:25])[C:16]=2[C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[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][CH3:25])[C:16]=2[C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22282031HCID 22282031, compound

Product 1

HCID 22281957HCID 22281957, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(tert-Butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl}-N-[3-(2-methoxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Preparation 18)(278 mg) was dissolved in dioxane, 1M sodium hydroxide solution (4 ml) was added and the reaction was stirred at reflux for 0.5 hours. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and 1M hydrochloric acid. The organic phase was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The product was purified on silica (10 g) eluting with a solvent gradient of pentane:ethyl acetate (1:0 to 6.4) to yield the title compound as a white solid (160 mg).

Workup

  1. temperatureat reflux for 0.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and 1M hydrochloric acid
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customThe product was purified on silica (10 g)
  8. washeluting with a solvent gradient of pentane:ethyl acetate (1:0 to 6.4)

Sources & evidence

ORD record
ord-85c7769c4b3e4afea9105f18079f283b
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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