Dimethyl Sulfoxide → HCID 118093956, Verbindung

HRID 1056970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056970
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O.[NH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 4082852-MorpholinoethylamineHCID 118093763HCID 118093763, Verbindung

Produkt 1

HCID 118093956HCID 118093956, VerbindungAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 1-bromo-4-fluoro-3-nitro-2-phenoxybenzene (0.057 g, 0.18 mmol) and cesium carbonate (0.0715 g, 0.220 mmol) in dimethyl sulfoxide (0.20 mL, 2.8 mmol) was treated with N-(2-aminoethyl)morpholine (0.0289 mL, 0.220 mmol) and stirred at 20° C. for 24 h, after which time the reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 100% EtOAc) gave the desired product (60 mg, 78%) a brown oil. LCMS calculated for C18H21BrN3O4 (M+H)+: m/z=422.1, 424.1. found: 422.1, 424.1.

Aufarbeitung

  1. customLayers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customPurification by flash column chromatography (100% hexanes to 100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a219e17b2a9a43b1ad34107382dede6b
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399640B2

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