Water → HCID 10498190, compound

HRID 654797Notes

Reaction equation

HRID 654797 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:23]#[N:24])=[N:9]2)=[CH:4][CH:3]=1.CI.[C:27](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:27][NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:23]#[N:24])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10712041HCID 10712041, compound

Product 1

HCID 10498190HCID 10498190, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-aminophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carbonitrile (1 g), methyl iodide (0.42 g) and potassium carbonate (0.6 g) in N,N-dimethylformamide (10 ml) was stirred at ambient temperature for 1 hour. The mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue (1.2 g) was purified by column chromatography on silica gel (20 g) eluting with chloroform to give crystals of 1-[4-(methylamino)phenyl]-5-[4-(methylsulfonyl)phenyl]pyrazole-3 -carbonitrile (0.31 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue (1.2 g) was purified by column chromatography on silica gel (20 g)
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-1d964c8872d6429ab0560d7ab9122477
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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