2-(Ethoxymethylene)propanedinitrile → 5-amino-1-tert-butyl-1H-pyrazole-4-carbonitrile

HRID 1736570Notes

Reaction equation

HRID 1736570 reaction equation
[C:1]([NH:5][NH2:6])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C(O[CH:13]=[C:14]([C:17]#[N:18])[C:15]#[N:16])C>C(O)C>[C:1]([N:5]1[C:17]([NH2:18])=[C:14]([C:15]#[N:16])[CH:13]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 81890tert-ButylhydrazineHCID 10942334Sodium Methoxide

Product 1

HCID 27974545-amino-1-tert-butyl-1H-pyrazole-4-carbonitrileYield 87.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of tert-butylhydrazine (40 g, 0.32 mol), sodium methoxide (18 g, 0.32 mol) and ethanol 150 ml) was added ethoxymethylene malononitrile (42 g, 0.32 mol). The reaction mixture was heated to reflux for 2 hours and the solvent was removed in vacuo. The residue was extracted with chloroform, washed with water and the organic layer was concentrated in vacuo to afford 46 g (87%) of 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile as a semi-solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customthe solvent was removed in vacuo
  4. extractionThe residue was extracted with chloroform
  5. washwashed with water
  6. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-c815d297dd404e33ac24f2dffda46db9
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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