Sodium ethoxide → Ethyl 6-(trifluoromethyl)picolinimidate

HRID 931142Notes

Reaction equation

HRID 931142 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[F:5][C:6]([F:16])([F:15])[C:7]1[N:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][CH:8]=1>C(O)C>[F:16][C:6]([F:15])([F:5])[C:7]1[N:12]=[C:11]([C:13](=[NH:14])[O:1][CH2:2][CH3:3])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 216966182-Cyano-6-(trifluoromethyl)pyridine

Product 1

HCID 89853792Ethyl 6-(trifluoromethyl)picolinimidateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (197 mg, 2.9 mmol) was added to a solution of 6-(trifluoromethyl)picolinonitrile (250 mg, 1.45 mmol) in ethanol (10 mL) at room temperature. The reaction mixture was stirred for 2 h. The solvent was removed under reduced pressure and the resulting residue was dissolved in dichloromethane, washed with water, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound (291 mg) which was used without further purification. MS (ES+) (M+H) 219.16

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44caa1e08ca84505a59c71049c7cd0b0
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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