Lawesson's reagent → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline-6-thiol

HRID 341843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341843
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16](O)[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C(C)=CC=CC=1>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([SH:31])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

Produkt 1

HCID 158384715,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline-6-thiolAusbeute 30,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A portion (5.55 g) of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol obtained in Example 4 was suspended in xylene (700 mL); following the addition of a Lawesson reagent (4.04 g), the suspension was heated under reflux for 30 min under an argon atmosphere. After standing to cool, the supernatant was concentrated under vacuum and the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate) to yield the titled compound as colorless crystals (0.91 g).

Aufarbeitung

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 30 min under an argon atmosphere
  3. temperatureto cool
  4. concentrationthe supernatant was concentrated under vacuum
  5. customthe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-507ae99047eb43cba06871e3f86b754e
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856334

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