1,1'-Carbonyldiimidazole → HCID 23320433, compound

HRID 280459Notes

Reaction equation

HRID 280459 reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[C:15]([OH:17])=O)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>CN(C=O)C>[C:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[N:6]=[CH:5][C:4]=1[C:15]([NH:33][CH:30]1[CH2:32][CH2:31]1)=[O:17])#[N:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 69828CyclopropylamineHCID 136541271-(4-Chlorophenyl)-5-cyano-1H-pyrazole-4-carboxylic acid

Product 1

HCID 23320433HCID 23320433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.47 g of 5-cyano-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid and 2.03 g of carbonyldiimidazole dissolved in 25 ml of DMF was stirred at room temperature for approximately 15 minutes. Seven milliliters of cyclopropylamine was next added to the reaction mixture which was allowed to stir for approximately 16 hours. The mixture was poured into 150 ml of ice water and the precipitated solid was collected by filtration. This solid was recrystallized from ethanol and dried to afford 1.86 g of 5-cyano-1-(4-chlorophenyl)-N-cyclopropyl-1H-pyrazole-4-carboxamide. MP=204°-206° C.

Workup

  1. stirringto stir for approximately 16 hours
  2. filtrationthe precipitated solid was collected by filtration
  3. customThis solid was recrystallized from ethanol
  4. customdried

Sources & evidence

ORD record
ord-e1a500e1607347af95f88d32dd703d08
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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