Potassium Hydroxide → ME1111

HRID 337347Notes

Reaction equation

HRID 337347 reaction equation
CC1C=CC(S([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N:19]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[N:20]2)(=O)=O)=CC=1.[OH-].[K+]>C(O)C.O>[CH3:25][C:21]1[CH:22]=[C:23]([CH3:24])[N:19]([C:13]2[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=2[OH:11])[N:20]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86703255HCID 86703255, compound

Product 1

HCID 60143882ME1111Yield 58.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To 199.6 mg of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-5-methylphenyl 4-methylbenzene sulfonate was added a solution in which 314 mg of potassium hydroxide was dissolved in 4 ml of ethanol and 4 ml of water, and the mixture was heated at reflux for 1 hour. To the reaction mixture was added 20 ml of water, and extracted with 20 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and purified using preparative thin-layer silica gel column chromatography (hexane:ethyl acetate=4:1), and after the desired fraction was dissolved in 1,4-dioxane, it was lyophilized to yield 66.2 mg of the title compound.

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted with 20 ml of ethyl acetate
  3. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. custompurified
  6. dissolutionafter the desired fraction was dissolved in 1,4-dioxane

Sources & evidence

ORD record
ord-42dd9fee2b714612b039070e7448b767
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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