Triethylamine → 1H-Pyrazole-4-carboxamide, 5-chloro-1-(3-chlorophenyl)-N-methyl-

HRID 1731262Notes

Reaction equation

HRID 1731262 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=O.[C:17](N1C=CN=C1)([N:19]1C=CN=C1)=O.Cl.CN.C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:19][CH3:17])=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 6364545Methylamine hydrochlorideHCID 13821933HCID 13821933, compound

Product 1

HCID 1757891H-Pyrazole-4-carboxamide, 5-chloro-1-(3-chlorophenyl)-N-methyl-Yield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.7 g of 5-chloro-1-(3-chlorophenyl)-1H-pyrazole-4-carboxylic acid and 5.4 g of carbonyldiimidazole in 150 ml DMF was stirred at room temperature for 20 minutes. Next, 3.0 g of methylamine hydrochloride and 4.4 g of triethylamine were added and the mixture was stirred at room temperature for 20 hours. The mixture was poured into ice water and the precipitated solid was collected by filtration and dried. The solid was recrystallized from toluene to provide 3.1 g of 5-chloro-1-(3-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide. Yield 50%. mp=163°-165° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried
  3. customThe solid was recrystallized from toluene

Sources & evidence

ORD record
ord-e00aaf0af2574905b4080e1f0c6ed877
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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