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Sodium hydride → N-Ethyl-N-[6-(((4-methoxypyridin-2-yl)methyl)oxy)-2,2-dimethylchroman-4-yl]methanesulfonamide

HRID 567064
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 567064
[CH3:1][C:2]1([CH3:20])[CH2:11][CH:10]([N:12]([CH2:17][CH3:18])[S:13]([CH3:16])(=[O:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:19])[CH:8]=2)[O:3]1.[H-].[Na+].Cl.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH2:32]Cl)[CH:27]=1>CC(N(C)C)=O>[CH2:17]([N:12]([CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:19][CH2:32][C:28]3[CH:27]=[C:26]([O:25][CH3:24])[CH:31]=[CH:30][N:29]=3)[CH:8]=2)[O:3][C:2]([CH3:1])([CH3:20])[CH2:11]1)[S:13]([CH3:16])(=[O:15])=[O:14])[CH3:18]
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 139233682-(Chloromethyl)-4-methoxypyridine hydrochlorideHCID 17786837N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide

Produkt 1

HCID 9802243N-Ethyl-N-[6-(((4-methoxypyridin-2-yl)methyl)oxy)-2,2-dimethylchroman-4-yl]methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374
Dimethylacetamide
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

0.58 g (1.9 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide (Example 1g) was stirred at 50° C. for 30 min with 0.15 g (5 mmol) of NaH (80%) in 40 ml of DMA. A solution of 0.4 g (2 mmol) of 4-methoxy-2-chloromethylpyridine hydrochloride in 5 ml of DMA was then added dropwise and the mixture was heated to 75° C. for 2 h. After reaction was complete, it was concentrated in vac., the residue was treated with ice water, the mixture was extracted with EA, the extract was dried and concentrated, and the residue was crystallized using diisopropyl ether. 0.5 g was obtained, m.p. 87-89° C.

Aufarbeitung

  1. customAfter reaction
  2. concentrationit was concentrated in vac
  3. addition, the residue was treated with ice water
  4. extractionthe mixture was extracted with EA
  5. customthe extract was dried
  6. concentrationconcentrated
  7. customthe residue was crystallized
  8. custom0.5 g was obtained

Quellen und Nachweise

ORD-Eintrag
ord-ad04de4d3e4840b5810b71797efbac5b
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06177449B1

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