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

HRID 280468Notes

Reaction equation

HRID 280468 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13]([C:15]1[N:19]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:18]=[CH:17][C:16]=1[C:24]([OH:26])=O)#[N:14].CN>CN(C=O)C>[C:13]([C:15]1[N:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[N:18]=[CH:17][C:16]=1[C:24]([NH:3][CH3:1])=[O:26])#[N:14]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 212472685-cyano-1-tert-butyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 1757871H-Pyrazole-4-carboxamide, 5-cyano-1-(1,1-dimethylethyl)-N-methyl-Yield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carbonyldiimidazole (2.5 grams, 0.015 mole) was added to a solution of 5-cyano-1-tert-butyl-1H-pyrazole-4-carboxylic acid (2.0 grams, 50.01 mole) in DMF. The solution was stirred at room temperature for twenty minutes. Aqueous methylamine (1.5 ml, 0.015 mole) was added and the reaction mixture was stirred at room temperature for 16 hours, then poured into ice-water. The product precipitated and was collected, dried, and recrystallized from ethanol, yielding 1.4 grams of 5-cyano-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide, m.p., 164°-166° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours
  2. customThe product precipitated
  3. customwas collected
  4. customdried
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0037c6156d3d4b64ad1a0dfb90e4b214
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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