Water → HCID 86661726, Verbindung

HRID 1020817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020817
[F:1][C:2]([F:8])([F:7])[O:3][CH2:4][CH2:5][OH:6].Cl[C:10]1[N:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13].C(O[K])(C)(C)C.O>CN(C=O)C.COCCOC.CCOC(C)=O>[Cl:20][C:16]1[C:17]([Cl:19])=[N:18][C:10]([O:6][CH2:5][CH2:4][O:3][C:2]([F:8])([F:7])[F:1])=[C:11]([CH:15]=1)[C:12]([NH2:14])=[O:13]

Komponenten

7

Edukt 4

HCID 962WaterHCID 179516872-(Trifluoromethoxy)ethan-1-olHCID 537509302,5,6-Trichloropyridine-3-carboxamideHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 86661726HCID 86661726, VerbindungAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 18463208dimethoxyethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of compound 2-(trifluoromethoxy)ethanol (9.5 mmol) in DMF/DME (20/50 mL) was added 2,5,6-trichloronicotinamide (2.1 g, 9.5 mmol) and tert-BuOK (1.30 g, 11.4 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was poured into 100 mL of cold water, diluted with 100 mL of EtOAc, the organic layer was separated and the aqueous phase was further extracted twice with EtOAc, the combined organic layers were washed with brine twice, dried over Na2SO4 and concentrated, the residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:0 to 5:1) to give 5,6-dichloro-2-(2-(trifluoromethoxy)ethoxy)nicotinamide (0.24 g, 8%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.31 (s, 1H), 7.97 (s, 1H), 7.59 (s, 1H), 4.62 (t, 2H, J=4.0 Hz), 4.51 (t, 2H, J=4.0 Hz).

Aufarbeitung

  1. customthe organic layer was separated
  2. extractionthe aqueous phase was further extracted twice with EtOAc
  3. washthe combined organic layers were washed with brine twice
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:0 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-47d9e8230fb6496c9f86d1d1c4697dbb
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716478B2

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