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Hydrochloric Acid → 2,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

HRID 1282419
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1282419
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:18][F:19])([CH2:16][F:17])[CH:3]=1.[C:20]([CH2:22][CH2:23][NH2:24])#[N:21].[I-].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.CN(C)[C:49](=[O:51])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]([CH2:22][CH2:23][NH:24][C:49]([C:2]1[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:18][F:19])([CH2:16][F:17])[CH:3]=1)=[O:51])#[N:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 16473-AminopropionitrileHCID 4875Potassium IodideHCID 11776TriphenylphosphineHCID 31374DimethylacetamideHCID 184244094-bromo-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran

Produkt 1

HCID 9950752
2,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-bromo-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran (1.73 g), 2-cyanoethylamine (1.44 g), potassium iodide (0.86 g), triphenylphosphine (26 mg), palladium acetate (11 mg) and N,N-dimethylacetamide (10 ml) was stirred under a CO atmosphere at 100° C. for 3 hours. To the reaction mixture, 2 N HCl was added and the precipitating crystals were recovered by filtration. To the recovered crystals, ethyl acetate was added and the insoluble matter was filtered off; the filtrate was washed with a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was recrystallized with an ethanol/water mixed solvent, thereby giving N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide (1.46 g) having a melting point of 129-131° C.

Aufarbeitung

  1. filtrationthe precipitating crystals were recovered by filtration
  2. additionTo the recovered crystals, ethyl acetate was added
  3. filtrationthe insoluble matter was filtered off
  4. washthe filtrate was washed with a saturated aqueous solution of sodium thiosulfate
  5. dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was recrystallized with an ethanol/water mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-b202dfddb9ef489a88d2ce1bb8e10769
Quelldatensatz
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06455708B1

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