2-Thiophenesulfonyl chloride → HCID 57901653, Verbindung

HRID 1851489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851489
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH3:17])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:17][O:16][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][S:23]([C:19]3[S:18][CH:22]=[CH:21][CH:20]=3)(=[O:25])=[O:24])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Komponenten

4

Edukt 2

HCID 855182-Thiophenesulfonyl chlorideHCID 15399415ethyl 7-amino-5-methoxy-1H-indole-2-carboxylate

Produkt 1

HCID 57901653HCID 57901653, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixed solution of ethyl 7-amino-5-methoxy-1H-indole-2-carboxylate (0.40 g) and pyridine (10 mL) was added 2-thiophenesulfonyl chloride (0.38 g) under ice-cooling, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=15:85-35:65), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (370 mg, yield 57%) as colorless needle crystals. melting point 158-159° C.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a12c6b160168497292c4616d56dae2e8
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957070B2

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