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

HRID 280453Notes

Reaction equation

HRID 280453 reaction equation
[C:1]([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:18]CC)=O)#[N:2].[CH3:21][NH2:22]>CN(C=O)C>[C:1]([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:22][CH3:21])=[O:18])#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13772947HCID 13772947, compound

Product 1

HCID 1757851H-Pyrazole-4-carboxamide, 5-cyano-1-(2,4-dichlorophenyl)-N-methyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.5 g of 5-cyano-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester in 20 ml of DMF was added 20 ml of 40% aqueous monomethylamine. The reaction mixture was stirred at room temperature for approximately two and one-half hours whereupon the solution was poured into ice water. The precipitate was collected by filtration and recrystallized from methanol/water to afford 1.3 g of 5-cyano-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide. MP=182°-183° C.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-2e3cb0474f3541759327311c45fbf182
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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