Sodium hydride → N-(2-chloro-3-nitropyridin-4-yl)-2,6-dichloro-4-cyanobenzamide

HRID 449904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449904
[H-].[Na+].[Cl:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([NH2:13])[CH:7]=[CH:6][N:5]=1.[Cl:14][C:15]1[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[C:20]([Cl:26])[C:16]=1[C:17](Cl)=[O:18]>CN(C=O)C>[Cl:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([NH:13][C:17](=[O:18])[C:16]2[C:20]([Cl:26])=[CH:21][C:22]([C:24]#[N:25])=[CH:23][C:15]=2[Cl:14])[CH:7]=[CH:6][N:5]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 109650142-Chloro-3-nitropyridin-4-amineHCID 866489562,6-Dichloro-4-cyanobenzoyl chloride

Produkt 1

HCID 86648955N-(2-chloro-3-nitropyridin-4-yl)-2,6-dichloro-4-cyanobenzamideAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

NaH (0.46 g, 11.6 mmol, 60% dispersion in mineral oil) was added in one portion to a cooled (0° C.) solution of 2-chloro-3-nitropyridin-4-amine (1.00 g, 5.8 mmol) in DMF (15 mL). The mixture was stirred for 20 mins and then a solution of 2,6-dichloro-4-cyanobenzoyl chloride (0.68 g, 2.9 mmol) in DMF (5 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 4 hours and then poured onto ice-water (20 mL). The resulting precipitate was collected by filtration and then the filtrate was extracted by EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was combined with previously collected precipirate and the material was purified by silica gel column chromatography (MeOH:CH2Cl2 1:10) to afford N-(2-chloro-3-nitropyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (0.5 g, yield: 23%). LCMS (ESI) m/z: 372.6 [M+H+]

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 0° C. for 4 hours
  2. additionpoured onto ice-water (20 mL)
  3. filtrationThe resulting precipitate was collected by filtration
  4. extractionthe filtrate was extracted by EtOAc (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customthe material was purified by silica gel column chromatography (MeOH:CH2Cl2 1:10)

Quellen und Nachweise

ORD-Eintrag
ord-e6505cfc747c49e3be36a8d1fe556d92
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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