Glycerol → HCID 19381206, Verbindung

HRID 2063543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063543
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10].[CH2:11](O)[CH:12](O)[CH2:13]O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[OH-].[Na+]>CS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]2[C:3]=1[N:10]=[CH:13][CH:12]=[CH:11]2

Komponenten

6

Edukt 4

HCID 753GlycerolHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 106318572-Bromo-4-ethylaniline

Produkt 1

HCID 19381206HCID 19381206, VerbindungAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6395Methanesulfonic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of 2-bromo-4-ethylphenylamine (1.6 g, 8.0 mmol), propane-1,2,3-triol (1.84 g, 2.5 equiv), FeSO4 (0.067 g, 0.30 equiv), 3-nitrobenzenesulfonic acid sodium salt (1.13 g, 0.63 equiv) in 4.5 mL of methanesulfonic acid was heated at 135° C. for 3 hours and then cooled to room temperature. 2 N Aqueous NaOH (˜40 mL) was added and the mixture was extracted with EtOAc (3×50 mL). The organic layer was washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel flash column chromatography using 5% to 20% EtOAc in hexane to afford the title compound as a black solid (1.3 g). MS (ES) m/z 235.9 (M+H+).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with EtOAc (3×50 mL)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-01baaf861b674837b307edb9a432574d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288373B2

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