Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methane | HCID 297 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 3,5-Dichloro-2-cyanopyridine | HCID 2769699 | — |
| Reactant | 2-Cyano-3,5-difluoropyridine | HCID 2783253 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 3,5-Difluoropicolinimidamide | HCID 10219565 | 39.1% |
Reaction Steps
33.4 g (0.624 mol) of ammonium chloride are suspended in 1 l of toluene and cooled to 0-5° C. 328 ml of trimethylaluminum (2 M in hexane, 0.624 mol) are added dropwise, and the mixture is stirred at RT until the evolution of methane has ceased. The solution of 3,5-dichloro-pyridine-2-carbonitrile in toluene (solution from Example V) is then added dropwise, and the mixture is then stirred at 80° C. overnight. After cooling to from 0 to −5° C., MeOH is added dropwise until the evolution of gas has ceased, the salts are filtered off with suction and washed to 2× with a little MeOH. The mixture is concentrated using a rotary evaporator and the residue is dissolved in 500 ml of CH2Cl2/MeOH (9:1) and once more filtered off with suction from inorganic salts. The mixture is concentrated using a rotary evaporator, giving 23.6 g (39.1%) of 3,5-difluoro-2-pyridinecarboximidamide as hydrochloride (m.p.: 183° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07514565B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-63d611a7a0054f5ea0c8f3c555882534 |
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| Source note | uspto-grants-2009_04 |
|---|
