Tetrahydrofuran → HCID 136060807, Verbindung

HRID 1851440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851440
[C:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])=[O:14])#[N:2].Cl.ON.C([N:26]([CH2:29]C)CC)C.[O:31]1CCCC1>O.CO>[O:31]1[CH:29]=[N:26][C:1]([C:3]2[NH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][C:6]=3[NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:15])=[N:2]1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 57901755HCID 57901755, Verbindung

Produkt 1

HCID 136060807HCID 136060807, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-(2-cyano-1H-indol-7-yl)thiophene-2-sulfonamide (0.50 g), hydroxyamine hydrochloride (0.17 g), triethylamine (0.83 mL), tetrahydrofuran (2 mL) and methanol (2 mL) was stirred at room temperature overnight. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried. A mixture of the obtained crystals and methyl orthoformate (10 mL) was heated under reflux for 4 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography. The title compound (0.18 g, yield 33%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point>185° C. (decomposition).

Aufarbeitung

  1. filtrationthe obtained crystals were filtrated
  2. washwashed with water
  3. customdried
  4. additionA mixture of the obtained crystals and methyl orthoformate (10 mL)
  5. temperaturewas heated
  6. temperatureunder reflux for 4 hr
  7. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-926696e7e2504b04ad96fbd2b0349d04
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957070B2

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