Methylamine → 5-chloro-N-methyl-1-phenylpyrazole-4-carboxamide

HRID 1731267Notes

Reaction equation

HRID 1731267 reaction equation
[Cl: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]([O:15]CC)=O.[CH3:18][NH2:19]>CN(C=O)C>[Cl: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:19][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 13608341Ethyl 5-chloro-1-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 1767335-chloro-N-methyl-1-phenylpyrazole-4-carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.5 g of 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester and 20 ml of 40% aqueous methylamine in 20 ml DMF was stirred at room temperature for about 45 hours. Thin layer chromatography showed mostly starting material so an additional 10 ml of 40% aqueous methylamine was added to the reaction mixture which was stirred for an additional 5 days. The reaction mixture was poured into ice water and the precipitated solid was collected by filtration. After drying, the solid was recrystallized from toluene to afford 2.3 g of 5-chloro-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. Yield 70%. mp=182°-183° C.

Workup

  1. additionwas added to the reaction mixture which
  2. filtrationthe precipitated solid was collected by filtration
  3. customAfter drying
  4. customthe solid was recrystallized from toluene

Sources & evidence

ORD record
ord-7a3d7abc47c5477eac7f7587a913bca6
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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