(1-Ethoxyethylidene)malononitrile → HCID 19432763, compound

HRID 1736534Notes

Reaction equation

HRID 1736534 reaction equation
Cl.[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[NH:8][NH2:9].C[O-].[Na+].C(O[C:16](=[C:18]([C:21]#[N:22])[C:19]#[N:20])[CH3:17])C>C(O)C>[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[N:8]1[C:21]([NH2:22])=[C:18]([C:19]#[N:20])[C:16]([CH3:17])=[N:9]1

Participants

5

Reactant 3

HCID 79450(1-Ethoxyethylidene)malononitrileHCID 10942334Sodium MethoxideHCID 19432785HCID 19432785, compound

Product 1

HCID 19432763HCID 19432763, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methylcyclopentylhydrazine hydrochloride (7.4 g, 48.8 mmol) in ethanol (100 ml) was added sodium methoxide (2.6 g, 48.8 mmol). The resulting white suspension was stirred for 10 minutes at room temperature and then (1-ethoxyethylidene)malononitrile (6.7 g, 48.8 mmol) was added. The reaction mixture was heated to reflux and was stirred for 5 hours. The solvent was removed in vacuo and the residue was partitioned between chloroform and water. The organic layer was separated and the aqueous layer was extracted with chloroform three times. The combined organic layers were washed with brine, then dried over anhydrous MgSO4. The solution was passed through a plug of silica gel and the solvent was removed in vacuo. The residue was washed with ether to afford 5.6 g (56%) of 1-(2-methylcyclopentyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile as a white powder, m.p. 158°-159° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. stirringwas stirred for 5 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between chloroform and water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with chloroform three times
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. customthe solvent was removed in vacuo
  11. washThe residue was washed with ether

Sources & evidence

ORD record
ord-d1c57a525cdc445c8526761567331e33
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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