Methane → HCID 10219565, compound

HRID 2121444Notes

Reaction equation

HRID 2121444 reaction equation
[Cl-].[NH4+].C[Al](C)C.C.ClC1C(C#N)=[N:11]C=C(Cl)C=1.[F:18][C:19]1[C:20]([C:26]#[N:27])=[N:21][CH:22]=[C:23]([F:25])[CH:24]=1>C1(C)C=CC=CC=1.CO>[F:18][C:19]1[C:20]([C:26](=[NH:11])[NH2:27])=[N:21][CH:22]=[C:23]([F:25])[CH:24]=1

Participants

8

Reactant 5

HCID 297MethaneHCID 25517Ammonium ChlorideHCID 27696993,5-Dichloro-2-cyanopyridineHCID 27832532-Cyano-3,5-difluoropyridine2×HCID 16682925Trimethylaluminum

Product 1

HCID 10219565HCID 10219565, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

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 trimethylaluminium (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.).

Workup

  1. additionis added dropwise until the evolution of gas
  2. filtrationthe salts are filtered off with suction
  3. washwashed to 2× with a little MeOH
  4. concentrationThe mixture is concentrated
  5. customa rotary evaporator
  6. dissolutionthe residue is dissolved in 500 ml of CH2Cl2/MeOH (9:1)
  7. filtrationonce more filtered off with suction from inorganic salts
  8. concentrationThe mixture is concentrated
  9. customa rotary evaporator

Sources & evidence

ORD record
ord-1d250d2bbce94bda92d0435e68cb1c96
Source dataset
uspto-grants-2004_02
Patent number
US06696451B1

Reaction notes

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