Triethylamine → HCID 899884, compound

HRID 1600820Notes

Reaction equation

HRID 1600820 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 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (1-ethoxyethylidene)malononitrile (68 g, 0.5 mol) and 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, then was cooled in ice and the product was collected by filtration and washed with ether to afford 85.9 g of 1-tert-butyl-3-methyl-5-amino-1H-pyrazole-4-carbonitrile 2/3 Et3N.HCl. An additional 46.2 g of the desired product was also obtained by concentration of the mother liquor and recrystallization of the residue from ethanol.

Workup

  1. temperaturewas cooled in ice
  2. filtrationthe product was collected by filtration
  3. washwashed with ether

Sources & evidence

ORD record
ord-9e3ec41a64094905a55a07fd8bab8b3d
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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