Potassium Iodide → 5-(2-Cyclopropyl-2-oxoethylamino)-2-fluoro-4-methylbenzonitrile

HRID 1773081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773081
[NH2:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:21][C:22]([CH:24]1[CH2:26][CH2:25]1)=[O:23]>CN(C)C=O>[CH:24]1([C:22](=[O:23])[CH2:21][NH:1][C:2]2[C:3]([CH3:11])=[CH:4][C:5]([F:10])=[C:6]([CH:9]=2)[C:7]#[N:8])[CH2:26][CH2:25]1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 109208412-Bromo-1-cyclopropylethan-1-oneHCID 866774495-Amino-2-fluoro-4-methylbenzonitrile

Produkt 1

HCID 866912475-(2-Cyclopropyl-2-oxoethylamino)-2-fluoro-4-methylbenzonitrileAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5-Amino-2-fluoro-4-methylbenzonitrile (12 g, 80 mmol) was dissolved in anhydrous N,N-dimethylformamide (160 mL) under nitrogen, and potassium carbonate (13.27 g, 96 mmol) and potassium iodide (14.61 g, 88 mmol) were added as solids with stirring. The reaction was stirred for 5 minutes at room temperature and then bromomethyl cyclopropylketone (20.24 mL, 180 mmol) was added. The reaction mixture was heated to 60° C. for 3 hours, and then the solvents removed under reduced pressure. The residue was dissolved in EA (400 mL) and washed with 400 mL of water. The organic layer was dried over magnesium sulfate, and solvent was removed under reduced pressure. The residue was re-dissolved in a minimum amount of EA, and hexanes were added to bring the solution to 3:1 hexanes: EA by volume. The product precipitated out of solution and was collected by filtration to provide 5-(2-cyclopropyl-2-oxoethylamino)-2-fluoro-4-methylbenzonitrile (14.19 g, 61.2 mmol). LC/MS (m/z: 233, M+1)

Aufarbeitung

  1. stirringThe reaction was stirred for 5 minutes at room temperature
  2. customthe solvents removed under reduced pressure
  3. dissolutionThe residue was dissolved in EA (400 mL)
  4. washwashed with 400 mL of water
  5. dry with materialThe organic layer was dried over magnesium sulfate, and solvent
  6. customwas removed under reduced pressure
  7. dissolutionThe residue was re-dissolved in a minimum amount of EA, and hexanes
  8. additionwere added
  9. customThe product precipitated out of solution
  10. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-b2286a80906d4060887b10d56b7abf73
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09254284B2

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