Water → 5-Bromo-3-(3-methoxypropyl)benzo[d]oxazol-2(3H)-one

HRID 216931

Reaktionsgleichung

Reaktionsgleichung von HRID 216931
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.CS(O[CH2:17][CH2:18][CH2:19][O:20][CH3:21])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[C:6]=2[CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 268532-Benzoxazolinone, 5-bromo-HCID 116939633-Methoxypropyl methanesulfonate

Produkt 1

HCID 595686035-Bromo-3-(3-methoxypropyl)benzo[d]oxazol-2(3H)-oneAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 5-bromobenzo[d]oxazol-2(3H)-one (1.1 g), 3-methoxypropyl methanesulfonate (1.297 g) and potassium carbonate (2.131 g) in acetonitrile (25 mL) was heated at 70° C. for 16 h. Water was added and the mixture was extracted with ethyl acetate (3 times). The organic layers were dried (MgSO4), evaporated and purified by flash chromatography (silica, isohexane-acetone (5:1) as eluent) to give the sub-titled compound (1.50 g) as an oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3 times)
  2. dry with materialThe organic layers were dried (MgSO4)
  3. customevaporated
  4. custompurified by flash chromatography (silica, isohexane-acetone (5:1) as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-fec2372dda034954aea9c090d9c7a41d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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