Triethylamine → HCID 899884, compound

HRID 2257049Notes

Reaction equation

HRID 2257049 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-2d75b0463f464ab9b1e609943074e7c8
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

Loading…