Dimethylformamide → 1H-Pyrazole-4-carboxamide, 5-cyano-N-methyl-1-phenyl-

HRID 279952Notes

Reaction equation

HRID 279952 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.[C-:18]#[N:19].[Na+].C[N:22]([CH:24]=O)C.CN>O>[C:18]([C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:13]([NH:22][CH3:24])=[O:15])#[N:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 8929Sodium CyanideHCID 13608341Ethyl 5-chloro-1-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 1636751H-Pyrazole-4-carboxamide, 5-cyano-N-methyl-1-phenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 100 ml 3-neck round bottom flask was charged with 12.0 g (0.048 mol) of 99.1% pure 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester, 4.7 g (0.096 mol) of sodium cyanide and 28.8 ml of DMF. The resulting mixture was heated at approximately 100° C. for 6 hours and then stirred at room temperature overnight. Thirteen grams (0.17 mol) of 40% aqueous methylamine were added to the reaction mixture dropwise. The reaction mixture was stirred at room temperature for 61/2 hours and 28.8 ml of water was added. The mixture was stirred for 30 minutes and the precipitated solid was collected by filtration. The resulting solid was washed with water and vacuum dried to afford 9.2 g of 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. The corrected yield was 73.4% and purity of the final product by high pressure liquid chromatography was 85.8%.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 30 minutes
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe resulting solid was washed with water and vacuum
  5. customdried

Sources & evidence

ORD record
ord-86267b547f5b4481a172f217c06b3af0
Source dataset
uspto-grants-1986_05
Patent number
US04587348

Reaction notes

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