Ethylamine → 5-bromo-1-phenyl-N-ethyl-1H-pyrazole-4-carboxamide

HRID 1731265Notes

Reaction equation

HRID 1731265 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(N1C=CN=C1)([N:18]1[CH:22]=[CH:21]N=C1)=O.C(N)C>CN(C=O)C>[Br:1][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:18][CH2:22][CH3:21])=[O:15]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 682631,1'-CarbonyldiimidazoleHCID 138219315-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 138219365-bromo-1-phenyl-N-ethyl-1H-pyrazole-4-carboxamideYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.6 g of 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid and 2.4 g of carbonyldiimidazole in 50 ml DMF was stirred at room temperature for 30 minutes. Five milliliters of 70% aqueous ethylamine was next added to the solution and the mixture was stirred for an additional two hours at room temperature. The reaction mixture was poured into ice water and the precipitated solid was collected by filtration. The solid was recrystallized from ethanol to afford 1.0 g of 5-bromo-1-phenyl-N-ethyl-1H-pyrazole-4-carboxamide. Yield 34%. mp=158°-160° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-29283ee7967e47b6ba6d7e8ac1caa042
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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