Diethyl Ether → HCID 131721159, Verbindung

HRID 1418296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1418296
[Cl:1][C:2]1[C:7](O)=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.[C:21](=[O:24])([O-])[O-].[K+].[K+].[CH3:27][C:28]1C(CC#C)=C(C=CC=1C)S([O-])(=O)=O.[Cl-].[NH4+].[CH2:44](OCC)C>C(#N)C>[Cl:1][C:2]1[C:7]([CH3:44])=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[C:3]=1[O:24][CH2:21][C:27]#[CH:28]

Komponenten

7

Edukt 5

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15390589HCID 15390589, VerbindungHCID 131721160HCID 131721160, Verbindung

Produkt 1

HCID 131721159HCID 131721159, VerbindungAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

An acetonitrile (10 mL) solution of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.21 g, 0.70 mmol), potassium carbonate (0.01 g, 0.7 mmol) and methylpropargyltosylate (0.17 g, 0.77 mmol) was stirred for 2.5 hours under reflux. A saturated ammonium chloride solution (10 mL) and diethyl ether (10 mL) were added to the resulting mixture, and the organic layer was separated and then the aqueous layer was extracted with diethyl ether (150 mL×2 times). The organic layer combined was washed with a saturated sodium chloride solution (15 mL) and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2) to obtain a white solid of 2-(4-chloro-2-fluoro-5-methylpropargyloxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.08 g, yield:32.9%).

Aufarbeitung

  1. temperatureunder reflux
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethyl ether (150 mL×2 times)
  4. washThe organic layer combined was washed with a saturated sodium chloride solution (15 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was evaporated
  9. customto give crude product, which
  10. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-5a3df2891f02421d8d81209bea689511
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05883049

Notizen zur Reaktion

Wird geladen…