Triethylamine → HCID 899884, compound

HRID 1736568Notes

Reaction equation

HRID 1736568 reaction equation
C(O[C:4](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH3:5])C.Cl.[C:12]([NH:16][NH2:17])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(O)C>[C:12]([N:16]1[C:9]([NH2:10])=[C:6]([C:7]#[N:8])[C:4]([CH3:5])=[N:17]1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79450(1-Ethoxyethylidene)malononitrileHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 899884HCID 899884, compoundYield 148.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of 1-ethoxyethylidene malononitrile (68.0 g, 0.5 mol), tert-butylhydrazine hydrochloride (62.3 g, 0.5 mol) in ethanol (500 ml) was added triethylamine (70 ml, 0.5 mol). The reaction mixture was stirred at room temperature for 2 hours, cooled in an ice-bath and a solid was collected by filtration and was washed with ether. The mother liquor was concentrated and the solid residue was recrystallized from ethanol. The two solid fractions were combined and dried at 65° C. in high vacuum for 24 hours to afford 132 g of 1-tert-butyl-3-methyl-5-amino-1H-pyrazole-4-carbonitrile as a white solid which is contaminated with triethylamine hydrochloride (approximately 2/3mol).

Workup

  1. temperaturecooled in an ice-bath
  2. filtrationa solid was collected by filtration
  3. washwas washed with ether
  4. concentrationThe mother liquor was concentrated
  5. customthe solid residue was recrystallized from ethanol
  6. customdried at 65° C. in high vacuum for 24 hours

Sources & evidence

ORD record
ord-e908cbfd4114403285472d6c9df2027f
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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