Methylamine → 1H-Pyrazole-4-carboxamide, 5-bromo-N-methyl-1-phenyl-

HRID 1731256Notes

Reaction equation

HRID 1731256 reaction equation
[Br:1][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]([OH:15])=O.[C:16](N1C=CN=C1)([N:18]1C=CN=C1)=O.CN>CN(C)C=O>[Br:1][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]([NH:18][CH3:16])=[O:15]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 138219315-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 1636761H-Pyrazole-4-carboxamide, 5-bromo-N-methyl-1-phenyl-Yield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Three grams of 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid and 2.6 g of carbonyldiimidazole were dissolved in 50 ml of dimethylformamide. The mixture was allowed to stir for 20 minutes and 7 ml of 40% aqueous methylamine was added to the reaction mixture. The mixture was stirred for 2 hours at room temperature and poured into ice water. The precipitated solid was collected by filtration and recrystallized from ethanol/water to afford 1.3 g of 5-bromo-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. Yield 42%. mp=157°-159° C.

Workup

  1. stirringThe mixture was stirred for 2 hours at room temperature
  2. filtrationThe precipitated solid was collected by filtration
  3. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-cf8f53efe0614f1b9771cca1cbb45ab8
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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