(1-Ethoxyethylidene)malononitrile → 5-Amino-3-methyl-1-(tetrahydro-3-furanyl)-1H-pyrazole-4-carbonitrile

HRID 1736564Notes

Reaction equation

HRID 1736564 reaction equation
Cl.[O:2]1[CH2:6][CH2:5][CH:4]([NH:7][NH2:8])[CH2:3]1.C[O-].[Na+].C(O[C:15](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[CH3:16])C>C(O)C>[O:2]1[CH2:6][CH2:5][CH:4]([N:7]2[C:20]([NH2:21])=[C:17]([C:18]#[N:19])[C:15]([CH3:16])=[N:8]2)[CH2:3]1

Participants

5

Reactant 3

HCID 79450(1-Ethoxyethylidene)malononitrileHCID 10942334Sodium MethoxideHCID 19432761(Tetrahydrofuran-3-yl)hydrazine hydrochloride

Product 1

HCID 194328185-Amino-3-methyl-1-(tetrahydro-3-furanyl)-1H-pyrazole-4-carbonitrileYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-tetrahydrofuranylhydrazine hydrochloride (6.2 g, 0.045 mol), sodium methoxide (2.4 g, 0.045 mol) and ethanol (70 ml) was refluxed under argon for 10 minutes. The reaction mixture was cooled to room temperature and 1-ethoxyethylidene malononitrile (6.1 g, 0.045 mol) was added. The reaction mixture was heated to reflux and stirred for 21 hours. The reaction was cooled and the solvent was removed in vacuo. The residue was recrystallized from water to afford 4.7 g (54%) of 1-(3-tetrahydrofuranyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile as yellow crystals, m.p. 134°-135° C. when dried at 90° C. in high vacuum.

Workup

  1. temperaturewas refluxed under argon for 10 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. temperatureThe reaction was cooled
  5. customthe solvent was removed in vacuo
  6. customThe residue was recrystallized from water

Sources & evidence

ORD record
ord-6c3a8bed5e294a16bfc559dc4b805d1c
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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