Water → HCID 86703256, compound

HRID 337349Notes

Reaction equation

HRID 337349 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[O:15][CH3:16])[N:3]=1.CI.[C:19](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:14]=[CH:13][C:11]([NH:12][CH3:19])=[CH:10][C:9]=2[O:15][CH3:16])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 4770939HCID 4770939, compound

Product 1

HCID 86703256HCID 86703256, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg of 4-(3,5-dimethyl-1H-pyrazol-1-yl)-3-methoxyaniline was dissolved in 6 ml of dimethylformamide, and 160 μl of methyl iodide and 636 mg of potassium carbonate were added and stirred at room temperature for 2.5 hours. To the reaction mixture, 50 ml of water was added and extracted with 50 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=1:3) to yield 48.7 mg of the title compound.

Workup

  1. extractionextracted with 50 ml of ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-f582db67486c486ab6874585dc76952f
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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