Ammonium Hydroxide → 1-(2,4-Dichlorophenyl)-5-(trifluoromethyl)-1h-pyrazole-4-carboxamide

HRID 1284403Notes

Reaction equation

HRID 1284403 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:6]=[CH:5][C:4]=1[C:16](O)=[O:17].C(N1C=CN=C1)([N:23]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[F:1][C:2]([F:20])([F:19])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:6]=[CH:5][C:4]=1[C:16]([NH2:23])=[O:17]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 13537979HCID 13537979, compound

Product 1

HCID 1904701-(2,4-Dichlorophenyl)-5-(trifluoromethyl)-1h-pyrazole-4-carboxamideYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Trifluoromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid (5.0 grams, 0.015 mole) and carbonyldiimidazole (2.74 grams, 0.017 mole) were dissolved in 35 ml of DMF. The solution was stirred for 10 minutes and ammonium hydroxide (8 ml) was then added. The reaction mixture was stirred at room temperature for 72 hours, then poured into 150 ml of ice/water. The product precipitated and was separated by filtration, dried, and recrystallized from toluene with charcoal, yielding 3.0 grams of 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxamide, mp=191°-193° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 72 hours
  2. customThe product precipitated
  3. customwas separated by filtration
  4. customdried
  5. customrecrystallized from toluene with charcoal

Sources & evidence

ORD record
ord-8e6f77f6c2fe4195b7ee7178a3de2dbb
Source dataset
uspto-grants-1986_01
Patent number
US04563210

Reaction notes

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