Tetrahydrofuran → HCID 178526691, Verbindung

HRID 22941

Reaktionsgleichung

Reaktionsgleichung von HRID 22941
O1CCCC1.[NH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1.C(N(CC)CC)C.Cl[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1>O>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([NH:6][C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)=[N:23][CH:24]=1)([O-:30])=[O:29]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 178511715HCID 178511715, Verbindung

Produkt 1

HCID 178526691HCID 178526691, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 150 ml of a tetrahydrofuran suspension containing 10 g of trans-4-aminocyclohexanol was added 15ml of triethylamine, 50 ml of a tetrahydrofuran solution containing 2-chloro-5-nitropyridine was further added thereto under ice-cooling, and then, the mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography (solvent: ethyl acetate-hexane (2:1)) to obtain 8.52 g of trans-4-(5-nitro-2-pyridylamino)cyclohexanol.

Aufarbeitung

  1. additionwas further added
  2. temperatureunder ice-cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel flash column chromatography (solvent: ethyl acetate-hexane (2:1))

Quellen und Nachweise

ORD-Eintrag
ord-bacd710fc5fe481bbf029ea3a08e93f4
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849622B2

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