Methyl morpholine oxide → 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide

HRID 45262

Reaktionsgleichung

Reaktionsgleichung von HRID 45262
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)CC=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:25]CC1.CCCCCC.[CH2:35]1C[O:38][CH2:37][CH2:36]1>CC(O)(C)C.O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH2:35][CH:36]([OH:25])[CH2:37][OH:38])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 82029Methyl morpholine oxideHCID 21883165Tetrahydrofuran hexaneHCID 244194826-chloro-N-phenyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide

Produkt 1

HCID 866597566-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittel2×

Versuchsvorschrift

To a solution of 1.3 g (4.2 mmol) of 6-chloro-N-phenyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide in 17 mL of a mixture (1/1) of tBuOH and water are added, at room temperature, 1.37 g (11.7 mmol) of NMO and 0.52 mL (0.04 mmol) of 2.5% OsO4 in tBuOH. Stirring is continued for 12 hours. The medium is then diluted with 200 mL of water and extracted with Et2O (2×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. 1.14 g of 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide are obtained in the form of an oil, which is used without further purification in the following step.

Aufarbeitung

  1. extractionextracted with Et2O (2×100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4e96f7796f8746948ad806fa4b810484
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541455B2

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