Phosphorus sulfide (P2S5) → 6,7-Dimethoxyquinoline-4(1H)-thione

HRID 853363

Reaktionsgleichung

Reaktionsgleichung von HRID 853363
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17].C(=O)(O)[O-].[Na+]>COCCOCCOC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=[S:17]

Komponenten

5

Edukt 3

HCID 14817Phosphorus sulfide (P2S5)HCID 4596116,7-Dimethoxy-4-hydroxyquinolineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 229368096,7-Dimethoxyquinoline-4(1H)-thioneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

After suspending the 6,7-dimethoxy-1H-quinolin-4-one (10.3 g, 50.0 mmol) described in WO9717329, phosphorus pentasulfide (26.7 g, 60.0 mmol) and sodium bicarbonate (26.7 g, 318 mmol) in diglyme (diethyleneglycol dimethyl ether) (100 ml), the suspension was heated and stirred at 80° C. for 2 hours. The reaction solution was returned to room temperature and poured into ice water (1000 ml), and the precipitated crystals were filtered out, washed with water and blow-dried to obtain the title compound (8.19 g, 37.0 mmol, 74%) as yellow crystals.

Aufarbeitung

  1. temperaturethe suspension was heated
  2. customwas returned to room temperature
  3. filtrationthe precipitated crystals were filtered out
  4. washwashed with water
  5. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-9b0baa9734fd4552981be5825d67b46d
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253286B2

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