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Ethyl Acetate → N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide

HRID 256606
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 256606
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[SH:14][C:15]1[CH:16]=[C:17]([C:21]2([O:27][CH3:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.[Cu]Cl.O>[CH3:28][O:27][C:21]1([C:17]2[CH:16]=[C:15]([S:14][C:2]3[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1
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Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 13920676N-(4-Iodophenyl)-N-methylmethanesulphonamideHCID 193757154-(3-Mercaptophenyl)-4-methoxytetrahydropyran

Produkt 1

HCID 19785586N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62652Cuprous chlorideKatalysator
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(4-iodophenyl)-N-methylmethanesulphonamide (0.31 g, 1 mmol), 4-(3-mercaptophenyl)-4-methoxytetrahydropyran (0.22 g), potassium carbonate (20 mg) and copper (I) chloride (30 mg) in DMF (20 ml) was heated to 140° C. and stirred for 3 hours. Ethyl acetate (40 ml) and water (40 ml) were added and the mixture was filtered through celite. The filtrate was washed with water (40 ml) and brine (40 ml), dried (MgSO4) and the solvent evaporated. The product was purified by column chromatography, thus N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide was obtained as an oil (0.12 g, 42%). NMR Spectrum 1.85-2.10 (4H, m), 2.85 (3H, s) 3.00 (3H, s), 3.30 (3H, s), 3.75-3.90 (4H, m), 7.25-7.35 (8H, m).

Aufarbeitung

  1. filtrationthe mixture was filtered through celite
  2. washThe filtrate was washed with water (40 ml) and brine (40 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated
  5. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-19103a9c9d644555b7ad090d95e37f36
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05258399

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