Triethylamine → HCID 67215740, Verbindung

HRID 472902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472902
Cl[C:2]([C:4]1[CH:5]=[CH:6][C:7]([N+:14]([O-:16])=[O:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:3].C(N(CC)CC)C.[CH:24]1[N:25]=[CH:26][N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=12>ClCCCl>[CH:24]1[N:25]=[C:26]([C:2]([C:4]2[CH:5]=[CH:6][C:7]([N+:14]([O-:16])=[O:15])=[C:8]([CH:13]=2)[C:9]([O:11][CH3:12])=[O:10])=[O:3])[N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=12

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 274090Imidazo(1,5-a)pyridineHCID 12350504Methyl 5-(chlorocarbonyl)-2-nitrobenzoate

Produkt 1

HCID 67215740HCID 67215740, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

5.6 g (0.023 mol) of methyl 5-(chlorocarbonyl)-2-nitrobenzoate and 3.4 ml (0.024 mol) of triethylamine are added to 1.3 g (0.011 mol) of imidazo[1,5-a]pyridine [described in J. Chem. Soc., (1955), 2834-2836] dissolved in 100 ml of 1,2-dichloroethane. The mixture is stirred at ambient temperature for 4 hours. The reaction medium is concentrated under reduced pressure and then the residue is taken up in dichloromethane and a saturated aqueous sodium bicarbonate solution. The organic phase is separated by settling, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The product is purified by column chromatography on silica gel, elution being carried out with dichloromethane. After evaporation, 3.1 g of a yellow solid are collected. Melting point: 151° C.; 1H NMR (d6-DMSO): 3.92 (3H, s), 7.39-7.42 (1H, m), 7.50-7.54 (1H, m), 8.00 (1H, s), 8.10 (1H, d), 8.25 (1H, d), 8.69 (1H, d), 8.76 (1H, s), 9.78 (1H, d)

Aufarbeitung

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. customThe organic phase is separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by column chromatography on silica gel, elution
  7. customAfter evaporation, 3.1 g of a yellow solid
  8. customare collected

Quellen und Nachweise

ORD-Eintrag
ord-9e40f5c0f7e54cba85f2fc9d6bf5482c
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633216B2

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