Sodium hydrosulfide → 7-Ethoxyquinoline-4(1H)-thione

HRID 965005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965005
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH3:14])=[CH:9][CH:10]=2)[N:5]=[C:4](Br)[CH:3]=1.[SH-:16].[Na+]>CO>[CH2:13]([O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2](=[S:16])[CH:3]=[CH:4][NH:5]2)=[CH:10][CH:9]=1)[CH3:14]

Komponenten

4

Edukt 2

HCID 28015Sodium hydrosulfideHCID 19075044HCID 19075044, Verbindung

Produkt 1

HCID 190750767-Ethoxyquinoline-4(1H)-thioneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-Chloro(bromo)-7-ethoxyquinoline (180 mg) and 70% sodium hydrosulfide (250 mg) were dissolved in methanol(50 ml) and refluxed for 15 hours. This reaction mixture was evaporated under reduced pressure and the residue was developed by silica gel column chromatography [Wako Gel™ C-200, mixed solution of methylene chloride with methanol (9 : 1)]. Fractions corresponding to yellow spots were collected and evaporated to obtain crude crystals. The obtained crude crystals were recrystallized from 40% aqueous ethanol solution to obtain 107 mg of the titled compound. Melting Point: 171°-174° C.; MS m/z: 205 (M+); NMR(DMSO-d6)δ: 1.40(3H, t, J=6.9 Hz), 4.15(2H, q, J=6.9 Hz), 7.02(1H, d, J=1.3 Hz), 7.09(1H, dd, J=2.3, 9.2 Hz), 7.15(1H, d, J=6.5 Hz), 7.73-7.78(1H, m), 8.58(1H, d, J=9.2 Hz), 12.68(1H, brs)

Aufarbeitung

  1. temperaturerefluxed for 15 hours
  2. customThis reaction mixture was evaporated under reduced pressure
  3. additionthe residue was developed by silica gel column chromatography [Wako Gel™ C-200, mixed solution of methylene chloride with methanol (9 : 1)]
  4. customFractions corresponding to yellow spots were collected
  5. customevaporated
  6. customto obtain crude crystals
  7. customThe obtained crude crystals
  8. customwere recrystallized from 40% aqueous ethanol solution

Quellen und Nachweise

ORD-Eintrag
ord-f967af128b16416e971d73ca0f925335
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773449

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