Triphosgene → 4-isocyanato-1H-indole

HRID 585947

Reaktionsgleichung

Reaktionsgleichung von HRID 585947
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[N:1]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)=[C:12]=[O:14]

Komponenten

4

Edukt 2

HCID 94429TriphosgeneHCID 5834314-Aminoindole

Produkt 1

HCID 220326444-isocyanato-1H-indoleAusbeute 187,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Aminoindole (0.5 g, 3.78 mmol) in toluene (50 mL) was treated with triphosgene (0.4 g, 1.35 mmol) and heated at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was taken up in diethyl ether, filtered, and the filtrate was concentrated under reduced pressure to provide title compound as yellow oil (0.4 g). 1H NMR (300 MHz, CDCl3-d6) δ 6.62 (m, 1H), 6.84 (d, 1H), 7.1 (t, 1H), 7.23 (m, 2H), 8.3 (s, 1H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ad8e1ecd286442d1b05e675857e1eecb
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933311B2

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