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Dimethyl Sulfoxide → HCID 22493624, Verbindung

HRID 986928
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 986928
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]1[C:13]([CH2:26][OH:27])=[N:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[C:20]=2[N:21]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CCCCCC.O>[CH3:11][C:12]1[C:13]([CH:26]=[O:27])=[N:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[C:20]=2[N:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22493589HCID 22493589, Verbindung

Produkt 1

HCID 22493624HCID 22493624, VerbindungAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel3×
HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A solution of 923 μl of dimethylsulfoxide in 2 ml of dichloromethane was added dropwise to a solution of 797 μl of oxalyl chloride in 6 ml of dichloromethane at −60° C. under a nitrogen gas stream, followed by stirring for 5 minutes. To the reaction mixture, a solution of 1 g of 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylquinoxaline-2-methanol in 6 ml of dichloromethane was added dropwise and the resulting mixture was stirred for 15 minutes. Triethylamine (4.8 ml) was then added dropwise to the reaction mixture, followed by stirring for 5 minutes. After the reaction mixture was raised to room temperature and stirred for 15 minutes, water was added thereto. The resulting mixture was extracted with dichloromethane. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 10% ethyl acetate/n-hexane), whereby 940 mg of the title compound were obtained in the form of a pale yellow solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. stirringby stirring for 5 minutes
  3. stirringstirred for 15 minutes
  4. extractionThe resulting mixture was extracted with dichloromethane
  5. washThe organic layer was successively washed with water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue so obtained

Quellen und Nachweise

ORD-Eintrag
ord-48576100cce34d05ba4ef450d73e7a79
Quelldatensatz
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06630463B2

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