1-Propanesulfonyl chloride → HCID 22176567, Verbindung

HRID 1797192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797192
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2]C.[OH:8][C:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])[CH2:10][NH2:11].[CH2:22]1CCN2C(=NCCC2)CC1>C(Cl)Cl>[OH:8][C:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])[CH2:10][NH:11][S:4]([CH:1]([CH3:2])[CH3:22])(=[O:5])=[O:6]

Komponenten

5

Edukt 3

HCID 662791-Propanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22176538HCID 22176538, Verbindung

Produkt 1

HCID 22176567HCID 22176567, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In a 500 mL, 3 neck flask fitted with a stirrer and thermometer, 2.98 g. of propanesulfonyl chloride was added dropwise to 3.92 g. of 2-hydroxy-2-(4-nitrophenyl)propylamine and 3.19 g. of DBU in CH2Cl2 (200 mL) while stirring at 0° C. under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred overnight at this temperature. In the morning, reaction was diluted with CH2Cl2 (100 mL) and the organic layer was washed two times with H2O, dried over Na2SO4, and concentrated under reduced vacuum to yield a viscous oil. This material was purified via silica gel chromatography employing the Water's Prep 2000 and eluting with a solvent of hexane/ethyl acetate 1:1 to yield the intermediate title compound (940 mg, 16%) as a viscous oil. Ion spray M.S. 302.1 (M*−1).

Aufarbeitung

  1. customIn a 500 mL, 3 neck flask fitted with a stirrer
  2. customIn the morning, reaction
  3. washthe organic layer was washed two times with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced vacuum
  6. customto yield a viscous oil
  7. customThis material was purified via silica gel chromatography
  8. washeluting with a solvent of hexane/ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-e65eeed6269842008f375406af99c4c0
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034045B1

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