Ammonium Chloride → Pyridazine-3-carboximidamide hydrochloride

HRID 433888Notes

Reaction equation

HRID 433888 reaction equation
C[O-].[Na+].[C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)#[N:5].[Cl-:12].[NH4+:13]>CO>[ClH:12].[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4](=[NH:13])[NH2:5])[N:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 13642940Pyridazine-3-carbonitrile

Product 1

HCID 18756080Pyridazine-3-carboximidamide hydrochlorideYield 55.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (25% w/v in methanol, 0.3 ml, 1.3 mmol) was added in one portion to a stirred solution of 3-cyanopyridazine (2.4 g g, 22.9 mmol) (Ref. Heterocycles, 1986, 24(3), 793) in methanol (10 ml). The resulting mixture was stirred at room temperature for 16 hours. Ammonium chloride (2.45 g, 45.8 mmol) was added to the reaction mixture, which was then stirred for 30 minutes before being ultrasonicated for a further 15 minutes. A fine, yellow precipitate was observed after this time. The solvent was evaporated under vacuum and the residue was suspended in ethanol (150 ml) and heated to reflux for 5 minutes. The hot mixture was filtered (gravity) to remove unreacted ammonium chloride and sodium chloride and was then cooled to room temperature. A pale yellow, crystalline solid formed upon cooling and this was isolated by suction filtration to give the title compound (2.03 g), m.p. 234°-241° C.

Workup

  1. stirringwas then stirred for 30 minutes
  2. custombefore being ultrasonicated for a further 15 minutes
  3. customThe solvent was evaporated under vacuum
  4. temperatureheated
  5. temperatureto reflux for 5 minutes
  6. filtrationThe hot mixture was filtered (gravity)
  7. customto remove unreacted ammonium chloride and sodium chloride
  8. temperaturewas then cooled to room temperature
  9. customA pale yellow, crystalline solid formed
  10. temperatureupon cooling
  11. customthis was isolated by suction filtration

Sources & evidence

ORD record
ord-4d38f28890454466b2bef50e1624ad75
Source dataset
uspto-grants-2003_12
Patent number
US06670362B2

Reaction notes

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