Water → HCID 67509783, compound

HRID 623493Notes

Reaction equation

HRID 623493 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N+:12]([O-])[CH:13]=1.CN(C)C(Cl)=O.O>C(#N)C>[CH3:7][C:8]1[C:13]([C:5]#[N:6])=[N:12][C:11]([O:15][CH2:16][C:17]([F:20])([F:18])[F:19])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl Chloride2×HCID 82115Trimethylsilyl cyanide2×HCID 67508942HCID 67508942, compound

Product 1

HCID 67509783HCID 67509783, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl cyanide (0.19 mL, 1.40 mmol) is added dropwise a solution of 5-methyl-2-(2,2,2-trifluoroethoxy)pyridine 1-oxide (0.14 g, 0.70 mmol, Step-2) and dimethylcarbamoyl chloride (0.1 mL, 1.05 mmol) in acetonitrile (10 mL) is stirred at room temperature for 2 days. Then trimethylsilyl cyanide (0.19 mL, 1.40 mmol) and dimethylcarbamoyl chloride (0.1 mL, 1.05 mmol) is added to the reaction mixture and refluxed with stirring for 20 hours. After cooling to room temperature, the reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1 to 1:1) to give 44 mg (29% yield) of the title compound as colorless oil.

Workup

  1. temperaturerefluxed
  2. stirringwith stirring for 20 hours
  3. temperatureAfter cooling to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-1ecbefbae6b74e5aa8e913d26a16d0ae
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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