Water → HCID 178434678, compound

HRID 17831

Reaction equation

HRID 17831 reaction equation
O.[NH2:2][NH2:3].C(O[C:7](=[C:9]([C:12]#[N:13])[C:10]#[N:11])[CH3:8])C.O>CCO>[NH2:11][C:10]1[NH:3][N:2]=[C:7]([CH3:8])[C:9]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 79450(1-Ethoxyethylidene)malononitrile

Product 1

HCID 178434678HCID 178434678, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Hydrazine monohydrate (6.8 ml, 0.14 mol) was dissolved in EtOH (10 ml) and cooled to 0° C. (1-Ethoxyethylidene)malononitrile (10 g, 0.073 mol) was added slowly and the mixture was heated at 95° C. for 2 h. After cooling to rt, water (20 ml) was added and the mixture was allowed to stand at rt overnight. The mixture was concentrated under reduced pressure and the resulting residue treated with EtOH (6 ml) and water (6 ml). After cooling in an ice/water bath for 10 min, the resulting precipitate was collected by filtration to give 6.34 g of 5-amino-3-methyl-1H-pyrazole-4-carbonitrile.

Workup

  1. additionwas added slowly
  2. temperatureAfter cooling to rt
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe resulting residue treated with EtOH (6 ml) and water (6 ml)
  5. temperatureAfter cooling in an ice/water bath for 10 min
  6. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-d69380414ccc4fa79cd8e846802ba5e2
Source dataset
uspto-grants-2010_06
Patent number
US07741318B2

Linked notes

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