p-Chlorothiophenol → HCID 67597008, Verbindung

HRID 1490306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1490306
FC(F)(F)S(O)(=O)=O.[Cl:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[C:12]2[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[O:23][C:11]1=2.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([SH:35])=[CH:31][CH:30]=1>C(OCCO)C.CCCCCC>[Cl-:9].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N+:13]([CH3:20])=[C:12]3[C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[O:23][C:11]=23)=[CH:31][CH:30]=1

Komponenten

5

Edukt 2

HCID 7815p-ChlorothiophenolHCID 86751471HCID 86751471, Verbindung

Produkt 1

HCID 67597008HCID 67597008, VerbindungAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 8076Glycol monoethyl etherLösungsmittel

Versuchsvorschrift

To a solution 11-chloro-5-methylbenzofuro[3, 2-b]quinoline trifluoromethanesulfonate from Example 56 (65 mg, 0.156 mmol) in 2-ethoxyethanol (5 ml) was added 4-chlorothiophenol (23 mg, 0.156 mmol) causing the reaction mixture to became a bright yellow. After 5-7 min, TLC showed the disappearance of the starting material. The reaction mixture was cooled to room temperature, diluted with hexane (100 mL), cooled below room temperature, filtered and dried to afford 50 mg (63%) of the title compound, mp 150°-151° C.; 1H NMR (CDCl3) δ 8.71 (d, 1H, J=7.6), 8.60 (s, 2H), 8.23 (s, 1H), 7.96 (s, 1H), 7.86 (t, 1H, J=6.8), 7.64 (m, 2H), 7.44-7.37 (m, 4H), 5.06 (s, 3H); 13C NMR (CDCl3) δ 159.65, 146.54, 140.91, 139.53, 137.16, 136.95, 136.13, 135.33, 135.10, 130.24, 129.26, 127.46, 126.74, 126.65, 126,48, 126.08, 119.23, 116.29, 113.54, 41.25; MS (FAB, m/z) 376 (M+).

Aufarbeitung

  1. temperaturecooled below room temperature
  2. filtrationfiltered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0a184aeb0f10460489d9ec4390f2be10
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681958

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