Dimethylformamide → 5-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole

HRID 628508Notes

Reaction equation

HRID 628508 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[CH:12][NH:11][N:10]=2)=[CH:5][C:4]=1[CH3:14].[CH3:15]N(C)C=O.[H-].[Na+].CI>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[CH:12][N:11]([CH3:15])[N:10]=2)=[CH:5][C:4]=1[CH3:14].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:15])[N:11]=[CH:12][CH:13]=2)=[CH:5][C:4]=1[CH3:14]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178488675HCID 178488675, compound

Product 2

HCID 1168691015-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazoleHCID 1182362533-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, to a mixture of 3-(4-methoxy-3-methyl-phenyl)-1H-pyrazole (described in Reference Preparation example 44) 5.38 g and N,N-dimethylformamide 100 ml was added 55% sodium hydride 1.5 g and the resulting mixture was stirred for a half hour and thereto was added methyl iodide 7.9 g. The resulting mixture was stirred for twelve hours and thereto was added water, and then the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 3-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole 2.9 g and 5-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole 1.0 g.

Workup

  1. stirringThe resulting mixture was stirred for twelve hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-f6d42db8ea6445028d413876ea8015e4
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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