Triethylamine → 5-bromo-1-phenyl-N,N-dimethyl-1H-pyrazole-4-carboxamide

HRID 1731264Notes

Reaction equation

HRID 1731264 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=[CH:19]1)=O.C(N(CC)CC)C.Cl.CNC>CN(C=O)C>[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]([N:18]([CH3:19])[CH3:16])=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 138219315-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 138219355-bromo-1-phenyl-N,N-dimethyl-1H-pyrazole-4-carboxamideYield 37%

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 was dissolved in 50 ml of DMF. The solution was stirred for 20 minutes and 2.3 g of triethylamine and 1.8 g of dimethylamine hydrochloride were added to the reaction mixture. The mixture was stirred at room temperature for 3 hours and was poured into ice water. The precipitated solid was collected by filtration and recrystallized from ethanol/water to afford 1.2 g of 5-bromo-1-phenyl-N,N-dimethyl-1H-pyrazole-4-carboxamide. Yield 37%. mp=79°-81° C.

Workup

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

Sources & evidence

ORD record
ord-79b6b029435543b2a330c20b14ee2374
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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