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Sodium Carbonate → HCID 67392848, Verbindung

HRID 908668
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 908668
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](B(O)O)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:20]1[S:21][C:22]2[C:28]([N+:29]([O-:31])=[O:30])=[C:27]([O:32][CH3:33])[CH:26]=[CH:25][C:23]=2[N:24]=1>O.COCCOC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:20]3[S:21][C:22]4[C:28]([N+:29]([O-:31])=[O:30])=[C:27]([O:32][CH3:33])[CH:26]=[CH:25][C:23]=4[N:24]=3)=[CH:9][C:4]=2[O:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 59659339HCID 59659339, Verbindung

Produkt 1

HCID 67392848HCID 67392848, VerbindungAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8071
1,2-Dimethoxyethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

0.697 g (4.2 mmol; 1.1 equivalent) of 1,3-benzodioxol-5-yl boronic acid as well as a solution of 1.2 g (11.35 mmol; 3 equivalents) of sodium carbonate in 15 ml of water are added to a suspension of 1.1 g (3.82 mmol) of 2-bromo-6-methoxy-7-nitro-1,3-benzothiazole and 133 mg (0.115 mmol; 0.03 equivalent) of palladium tetrakis-triphenylphosphine in 30 ml of 1,2-dimethoxyethane. The reaction mixture is maintained under stirring at 90° C. for 4 hours, then after concentration under reduced pressure, 100 ml of ethyl acetate is added to the medium which is then washed with twice 75 ml of a solution of water saturated with sodium chloride. The organic phase is dried over sodium sulphate then the solvents are evaporated off under reduced pressure and the residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane mixture 1:2). 0.960 g (yield of 76%) of 2-(1,3-benzodioxol-5-yl)-6-methoxy-7-nitro-1,3-benzothiazole is obtained in the form of beige powder.

Aufarbeitung

  1. temperatureThe reaction mixture is maintained
  2. concentrationafter concentration under reduced pressure, 100 ml of ethyl acetate
  3. additionis added to the medium which
  4. washis then washed with twice 75 ml of a solution of water saturated with sodium chloride
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customthe solvents are evaporated off under reduced pressure
  7. customthe residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane mixture 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-46daa666300747d6b6806ea303055c7f
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08017637B2

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