Cesium carbonate → 4-[3-(4-Phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

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Reaktionsgleichung

Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][C:7]=1[CH2:19][CH2:20][CH3:21].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:30])=[O:31])=[CH:25][CH:24]=2)=[C:7]([CH2:19][CH2:20][CH3:21])[CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 1-(3-bromopropoxy)-4-phenoxy-2-propylbenzene (1.01 g, 2.9 mmol) and 4-hydroxybenzenesulfonamide (0.5 g, 2.9 mmol) in dry DMF (29 mL) was added cesium carbonate (1.04 g, 3.2 mmol). The resulting suspension was stirred in a 50° C. oil bath for 5 h. After cooling to room temperature, the reaction suspension was concentrated under vacuum to a residue, which was then partitioned between ethyl acetate and water. The ethyl acetate phase was dried over sodium sulfate, filtered, and concentrated to an oil. The oil was chromatographed over silica gel with hexanes/ethyl acetate (2:1) to isolate the title compound.,

Aufarbeitung

temperatureAfter cooling to room temperature
concentrationthe reaction suspension was concentrated under vacuum to a residue, which
customwas then partitioned between ethyl acetate and water
dry with materialThe ethyl acetate phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated to an oil
customThe oil was chromatographed over silica gel with hexanes/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag: ord-4ddb90c180544ec590aee33b3ce03c91
Quelldatensatz: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07319170B2

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