Sodium hydride → HCID 89181156, Verbindung

HRID 595176

Reaktionsgleichung

Reaktionsgleichung von HRID 595176
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17](Cl)[N:16]=1>C1COCC1.O>[Cl:21][C:19]1[CH:20]=[C:15]([Cl:14])[N:16]=[C:17]([NH:9][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:8]=[CH:7][N:6]=2)[CH:18]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 27665Pyridine, 2,4,6-trichloro-HCID 27783152-Amino-4-(trifluoromethyl)pyridine

Produkt 1

HCID 89181156HCID 89181156, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 4-(trifluoromethyl)pyridin-2-amine (3.24 g, 20.0 mmol) and sodium hydride (1.2 g, 30 mmol) in THF (60 mL) was stirred at 0° C. under nitrogen for 1 hour, and then 2,4,6-trichloropyridine (3.62 g, 20.0 mmol) was added. The reaction was stirred at 25° C. for 3 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give 4,6-dichloro-N-[4-(trifluoromethyl)pyridin-2-yl]pyridin-2-amine. MS ESI calc'd. for C11H7Cl2F3N3 [M+H]+ 308. found 308. 1H NMR (400 MHz, CD3OD): δ 8.49 (d, J=5.6 Hz, 1H), 7.99 (s, 1H), 7.87 (s, 1H), 7.19 (d, J=1.2 Hz, 1H), 7.05 (d, J=1.2 Hz, 1H).

Aufarbeitung

  1. stirringThe reaction was stirred at 25° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-7e65cb70ad374ef5a9c6d773e7532239
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

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