Triethylamine → HCID 19432844, compound

HRID 487279Notes

Reaction equation

HRID 487279 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].[CH2:18](N(CC)CC)C>C(O)C>[C:12]([N:16]1[C:9]([NH2:10])=[C:6]([C:7]#[N:8])[C:4]([CH2:5][CH3:18])=[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 19432844HCID 19432844, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-ethoxyethylidene malononitrile (60.0 g, 0.4 mol), tert-butylhydrazine hydrochloride (50.0 g, 0.4 mol) and ethanol (500 ml) was heated to reflux. The heat was removed and triethylamine (55.8 ml, 0.4 mol) was added dropwise at such a rate as to maintain a gentle reflux. The reaction mixture was refluxed for an additional 1 hour, cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in ethyl acetate (300 ml) and washed with water (200 ml). The organic layer was separated, washed with brine and dried over sodium sulfate. The solvent was removed in vacuo to afford 75.6 g (67%) of 1-tert-butyl-3-ethyl-5-amino-1H-pyrazole-4-carbonitrile.

Workup

  1. temperaturewas heated to reflux
  2. customThe heat was removed
  3. temperatureto maintain a gentle reflux
  4. temperatureThe reaction mixture was refluxed for an additional 1 hour
  5. customthe solvent was removed in vacuo
  6. washwashed with water (200 ml)
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over sodium sulfate
  10. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-03f1b082ab7344eab12a88fca0835b1e
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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