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Dimethyl Sulfoxide → 4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3-ethyl-N,N-diisopropylpyridine-2-carboxamide

HRID 31715
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 31715
CS(C)=O.Cl[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([N:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[O:13])[C:7]=1[CH2:21][CH3:22].[H-].[Na+].[CH3:25][C:26]1([CH3:34])[O:31][CH2:30][CH:29]([CH2:32][OH:33])[CH2:28][O:27]1>C(OCC)(=O)C>[CH3:25][C:26]1([CH3:34])[O:31][CH2:30][CH:29]([CH2:32][O:33][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([C:12]([N:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[O:13])[C:7]=2[CH2:21][CH3:22])[CH2:28][O:27]1
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Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 597924654-chloro-3-ethyl-N,N-diisopropylpyridine-2-carboxamide

Produkt 1

HCID 597925594-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3-ethyl-N,N-diisopropylpyridine-2-carboxamideAusbeute 36,9 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a dimethylsulfoxide (20 ml) solution of the 4-chloro-3-ethyl-N,N-diisopropylpyridine-2-carboxamide (1 g, 3.72 mmol) obtained in the step (92b) above, oily sodium hydride, in oil (195 mg, 4.46 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, the (2,2-dimethyl-1,3-dioxan-5-yl)methanol (598 mg, 4.09 mmol) obtained in Example (11a) was added and the mixture was stirred at room temperature for 16.5 hours. Ethyl acetate was added to the reaction mixture. The mixture was washed twice with a saturate saline solution. The organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated. The residue was washed with diethyl ether to obtain the title compound (520 mg, yield: 36.9%) as a light yellow solid.

Aufarbeitung

  1. additionwas added at room temperature
  2. washThe mixture was washed twice with a saturate saline solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. washThe residue was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-faf7a348652c48d4ac613a0eb85291d2
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07425634B2

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