N-Methylethylamine → HCID 13654128, compound

HRID 280457Notes

Reaction equation

HRID 280457 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)(N1C=CN=C1)=[O:2].[C:13]([C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=2)[N:18]=[CH:17][C:16]=1C(O)=O)#[N:14].C(NC)C>CN(C=O)C>[C:13]([C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=2)[N:18]=[CH:17][C:16]=1[C:1]([N:8]([CH3:9])[CH2:12][CH3:11])=[O:2])#[N:14]

Participants

5

Reactant 3

HCID 12219N-MethylethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 13654126HCID 13654126, compound

Product 1

HCID 13654128HCID 13654128, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Two grams of carbonyldiimidazole was added to a solution of 2.0 g of 5-cyano-1-(3-cyanophenyl)-1H-pyrazole-4-carboxylic acid dissolved in 50 ml of DMF. The reaction mixture was stirred at room temperature for approximately 25 minutes whereupon 740 mg of N-ethyl-N-methylamine was added. The reaction mixture was allowed to stir for an additional 24 hours at which point the solution was poured into ice water. The precipitate solid was collected by filtration and dried to provide 1.2 g of 5-cyano-1-(3-cyanophenyl)-N-methyl-N-ethyl-1H-pyrazole-4-carboxamide following recrystallization from ethanol. MP=185°-187° C.

Workup

  1. additionwas added
  2. filtrationThe precipitate solid was collected by filtration
  3. customdried
  4. customto provide
  5. custom1.2 g of 5-cyano-1-(3-cyanophenyl)-N-methyl-N-ethyl-1H-pyrazole-4-carboxamide following recrystallization from ethanol

Sources & evidence

ORD record
ord-4730c5b888064bc5bb7542fe5a0b37cd
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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