Water → HCID 86648966, Verbindung

HRID 449931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449931
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([F:9])=[CH:4][N:3]=1.[H-].[Na+].[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:14]=1[C:15](Cl)=[O:16].O>CN(C)C=O>[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:14]=1[C:15]([NH:8][C:6]1[C:5]([F:9])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)=[O:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 222840352-Chloro-5-fluoropyridin-4-amine

Produkt 1

HCID 86648966HCID 86648966, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 2-chloro-5-fluoropyridin-4-amine (200 mg, 1.36 mmol) in dry N,N-dimethylformamide (10 mL) was added sodium hydride (65.5 mg, 2.73 mmol) in one portion at room temperature under N2. The reaction mixture was then stirred for 15 min and then a solution of 2,4,6-trichlorobenzoyl chloride (320 uL, 2.0 mmol) in N,N-dimethylforamide (400 uL) was added dropwise. The mixture was stirred at room temperature for 10 mins, and then poured into water (30 mL). The mixture was extracted with ethyl acetate (2×50 mL), and combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-5% methanol/dichloromethane) to give 2,4,6-trichloro-N-(2-chloro-5-fluoropyridin-4-yl)benzamide (260 mg, yield: 54%). 1H NMR (DMSO-d6, 400 MHz): δ 11.52 (s, 1H), 8.49 (s, 1H), 8.33 (d, J=5.5 Hz, 1H), 7.84 (s, 2H). LCMS (ESI) m/z: 354.9 [M+H+].

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 10 mins
  2. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  3. dry with materialwere dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (0-5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-455a57e465824bbba265bccdfbc90eb0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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