Sodium Hydroxide → HCID 22281957, compound

HRID 1062745Notes

Reaction equation

HRID 1062745 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 (278 mg) (Preparation 36) 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 (25 ml) and 1M hydrochloric acid (25 ml). The organic phase was separated, dried over magnesium sulphate and thesolvent removed under reduced pressure. The product was purified on silica (10 g) eluting with a solvent gradient of pentane:ethyl acectate (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 (25 ml) and 1M hydrochloric acid (25 ml)
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulphate
  6. customthesolvent removed under reduced pressure
  7. customThe product was purified on silica (10 g)
  8. washeluting with a solvent gradient of pentane

Sources & evidence

ORD record
ord-106b9e2a56d14af4a530b094a50e3d84
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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