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Sodium hydride → N-(6-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]pyrid-3-yl}-N-methylmethanesulphonamide

HRID 256610
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 256610
[H-].[Na+].Cl[C:4]1[N:9]=[CH:8][C:7]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[SH:16][C:17]1[CH:18]=[C:19]([C:23]2([O:29][CH3:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1>CN(C=O)C>[CH3:30][O:29][C:23]1([C:19]2[CH:18]=[C:17]([S:16][C:4]3[N:9]=[CH:8][C:7]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 193757154-(3-Mercaptophenyl)-4-methoxytetrahydropyranHCID 19785594N-(6-chloropyrid-3-yl)-N-methylmethanesulphonamide

Produkt 1

HCID 19743039N-(6-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]pyrid-3-yl}-N-methylmethanesulphonamideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Sodium hydride (79 mg, 50% dispersion in mineral oil, 1.65 mmol) was added to a solution of N-(6-chloropyrid-3-yl)-N-methyl-methanesulphonamide (0.33 g) and 4-(3-mercaptophenyl)-4-methoxytetrahydropyran (0.34 g) in DMF (10 ml). The mixture was stirred at ambient temperature for 15 minutes and heated at 140° C. for 1.5 hours. After cooling, it was partitioned between water (75 ml) and ethyl acetate (75 ml). The organic phase was washed with brine (50 ml), dried (MgSO4) and the solvent evaporated. The product was purified by column chromatography to give N-(6-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]pyrid-3-yl}-N-methylmethanesulphonamide as a gum (0.25 g, 41%).

Aufarbeitung

  1. temperatureheated at 140° C. for 1.5 hours
  2. temperatureAfter cooling
  3. customit was partitioned between water (75 ml) and ethyl acetate (75 ml)
  4. washThe organic phase was washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6594e3b162894be181d48e52cb146b5a
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05258399

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