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

HRID 1731266Notes

Reaction equation

HRID 1731266 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)(N1C=CN=C1)=O.C(N(CC)CC)C.Cl.[CH3:36][O:37][NH2:38]>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]([NH:38][O:37][CH3:36])=[O:15]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 521874O-Methylhydroxylamine hydrochloride2×HCID 138219315-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 138219375-bromo-1-phenyl-N-methoxy-1H-pyrazole-4-carboxamideYield 34.7%

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 60 ml DMF was stirred at room temperature for 30 minutes. Two grams of triethylamine and 1.7 g of methoxyamine hydrochloride were added to the solution. The mixture was stirred at room temperature for 24 hours and another equivalent of triethylamine and methoxyamine hydrochloride were added. The mixture was heated on the steam bath for two hours and poured into ice water. The precipitated solid was collected by filtration and recrystallized from ethanol to afford 1.0 g of 5-bromo-1-phenyl-N-methoxy-1H-pyrazole-4-carboxamide. Yield 34%. mp=194°-197° C.

Workup

  1. temperatureThe mixture was heated on the steam bath for two hours
  2. filtrationThe precipitated solid was collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3906111bfe2e4b93aa1819dcdad19618
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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