Sodium Azide → 4-Azido-5-chloropyridine-3-carbaldehyde

HRID 626705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626705
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10])=[N+:12]=[N-:13]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 595965804,5-Dichloropyridine-3-carbaldehyde

Produkt 1

HCID 866970494-Azido-5-chloropyridine-3-carbaldehydeAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4,5-dichloropyridine-3-carbaldehyde (6.78 g, 38.5 mmol) and sodium azide (2.62 g, 40.4 mmol) in DMF (25 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine (250 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane) to afford the title compound as a yellow solid (6.7 g, 96% yield). 1H NMR (400 MHz, CDCl3): δ 10.36 (s, 1H), 8.84 (s, 1H), 8.65 (s, 1H).

Aufarbeitung

  1. customThe reaction mixture was quenched with brine (250 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane)

Quellen und Nachweise

ORD-Eintrag
ord-6bfcfd0dc6364ef3a2a4de86f0e0f2bc
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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