2-Bromoethanol → HCID 86679483, Verbindung

HRID 1776525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776525
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=2[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.Br[CH2:22][CH2:23][OH:24].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=2[N:16]([CH2:22][CH2:23][OH:24])[S:17]([CH3:20])(=[O:19])=[O:18])[C:9]([O:11][CH3:12])=[O:10])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 59443764Methyl 3-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate

Produkt 1

HCID 86679483HCID 86679483, VerbindungAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of methyl 3-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate (1 g, 3.34 mmol), 2-bromoethanol (0.835 g, 6.68 mmol), and K2CO3 (0.923 g, 6.68 mmol) in CH3CN (12 ml) was heated at 110° C. under microwave irradiation for 12 hours. After cooling the solvent was evaporated and the residue was dissolved in EtOAc and filtered; the solvent was evaporated and the residue was purified by flash chromatography (eluent: EtOAc/petroleum ether 1/1) to give methyl 3-(cyclopropylmethoxy)-4-(N-(2-hydroxyethyl)methylsulfonamido)benzoate as a light brown oil (0.764 g, 2.225 mmol, 66.6% yield, /ESI+ 365.9 [MNa]+).

Aufarbeitung

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customthe residue was purified by flash chromatography (eluent: EtOAc/petroleum ether 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-bf0f0b2d6e874e88aa296fdad535a015
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265768B2

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