Methylamine → 1H-Pyrazole-4-carboxamide, 1-(2,4-dichlorophenyl)-N-methyl-5-(trifluoromethyl)-

HRID 1731274Notes

Reaction equation

HRID 1731274 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:21](N1C=CN=C1)([N:23]1C=CN=C1)=O.CN>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]([NH:23][CH3:21])=[O:17]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 13537979HCID 13537979, compound

Product 1

HCID 1636811H-Pyrazole-4-carboxamide, 1-(2,4-dichlorophenyl)-N-methyl-5-(trifluoromethyl)-Yield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Trifluoromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid (1.50 grams, 0.0046 mole) and carbonyldiimidazole (0.94 gram, 0.0058 mole) were dissolved in DMF. The reaction mixture was stirred for 10 minutes, then 7 ml. of 40% aqueous methylamine were added. The reaction mixture was stirred for three hours at room temperature, then poured into 150 ml. of water and filtered. The precipitate was dried to 1.51 grams, then recrystallized from 10:1 cyclohexane/toluene, yielding 1.23 grams of 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide, mp=143°-144° C.

Workup

  1. stirringThe reaction mixture was stirred for three hours at room temperature
  2. additionpoured into 150 ml
  3. filtrationof water and filtered
  4. customThe precipitate was dried to 1.51 grams
  5. customrecrystallized from 10:1 cyclohexane/toluene

Sources & evidence

ORD record
ord-232fd69398364414b2ae6faaa0fe97a5
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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