Trifluoromethanesulfonic acid → HCID 18930391, Verbindung

HRID 1464668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464668
[F:1][C:2]([F:8])([F:7])[S:3](O)(=O)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.FC(F)(F)SCl>C(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:17]=2[S:3][C:2]([F:8])([F:7])[F:1])=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 62406Trifluoromethanesulfonic acidHCID 67900Methanesulfenyl chloride, trifluoro-HCID 18930419Methyl 5-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 18930391HCID 18930391, VerbindungAusbeute 902,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Trifluoromethanesulfonic acid (0.27 g, 0.001795 mol) is added to a solution of methyl 5-(p-chlorophenyl)pyrrole-2-carboxylate (4.23 g, 0.01795 mol) in methylene chloride (70 mi) at -30° C. This mixture is treated with trifluoromethylsulfenyl chloride (4.0 g, 0.0293 mol), stirred for 30 minutes at -15° C., warmed to room temperature with stirring for three hours, diluted with methylene chloride, washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title product as an off-white solid (5.44 g, mp 133°-137° C.) which is identified by 1HNMR spectral analysis.

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringwith stirring for three hours
  3. washwashed with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-00a9a22d06cf41818bdf98bfba73226a
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306827

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