Methyl iodide → (E)-2,2,2-trifluoro-N-methoxy-1-(1-methylpyridin-1-ium-3-yl)ethanimine iodide

HRID 1034207Notes

Reaction equation

HRID 1034207 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](\[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)/[C:5]([F:8])([F:7])[F:6].[CH3:15][I:16]>C(#N)C>[I-:16].[CH3:1][O:2]/[N:3]=[C:4](\[C:9]1[CH:10]=[N+:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1)/[C:5]([F:8])([F:6])[F:7]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 140371602(1E)-2,2,2-Trifluoro-N-methoxy-1-(pyridin-3-yl)ethan-1-imine

Product 1

HCID 140371600(E)-2,2,2-trifluoro-N-methoxy-1-(1-methylpyridin-1-ium-3-yl)ethanimine iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

E-3-(α,α,α-Trifluoroacetyl)pyridine-O-methyl oxime (D7) (6.16 g, 0.030 mol) was treated with methyl iodide (15 ml, 0.241 mol) in acetonitrile (100 ml) at reflux for 3 h. The reaction mixture was cooled and evaporated to give a gum which was triturated with ether to give the title compound (D10) as a yellow solid (10.44 g, 100%) m.p. 119°-124° C.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customto give a gum which
  5. customwas triturated with ether

Sources & evidence

ORD record
ord-d827104476aa4650b2af8d13c398b6f0
Source dataset
uspto-grants-1994_05
Patent number
US05314901

Reaction notes

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