Butyl bromide → Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 348977

Reaktionsgleichung

[I:1][C:2]1[C:11]2[O:10][CH2:9][C:8](=[O:12])[NH:7][C:6]=2[CH:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH3:27]>CS(C)=O.O>[CH2:24]([N:7]1[C:6]2[CH:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=[C:2]([I:1])[C:11]=2[O:10][CH2:9][C:8]1=[O:12])[CH2:25][CH2:26][CH3:27]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of Methyl 8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (2.64 g) and potassium carbonate (5 g) in DMSO (20 mL) was added bromobutane (5 g), and the reaction mixture was stirred for 1 h at 80° C. The mixture was cooled to room temperature, diluted with 1:1 ethyl acetate/hexanes (100 mL) and water (160 mL), and separated. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes) afforded 2.24 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 8.13, 7.63, 4.74, 3.96, 3.92, 1.64, 1.42, 0.97.

Aufarbeitung

temperatureThe mixture was cooled to room temperature
customseparated
washThe organic layer was washed with water, and brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-453d63c5ea824b89aa84c6f2140e1f31
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07176242B2

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