Sodium hydride → HCID 20135081, Verbindung

HRID 580397

Reaktionsgleichung

Reaktionsgleichung von HRID 580397
[H-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][C:11]2[CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=[CH:25][C:10]=2[NH:9][C:8]1=[O:30])=[O:6].Br[CH2:32][O:33][CH3:34]>CN(C)C=O>[CH3:3][O:4][C:5]([CH:7]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][C:11]2[CH:22]=[C:23]([C:26]([F:29])([F:27])[F:28])[CH:24]=[CH:25][C:10]=2[N:9]([CH2:32][O:33][CH3:34])[C:8]1=[O:30])=[O:6]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 201350951,3,4,5-Tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one

Produkt 1

HCID 20135081HCID 20135081, VerbindungAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (360 mg; 7.5 mmole; 50% oil dispersion/prewashed with dry ether several times) in dry dimethylformamide (30 ml), cooled at 0°-5° C. was added a solution of 1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one (1.9 g; 5 mmole) in dry dimethylformamide (15 ml) dropwise and with stirring. The mixture was stirred for an additional 20 minutes at 0°-5° C., whereupon bromomethylmethyl ether (800 μl; 10 mmole) was added dropwise, and stirring was continued at this temperature for an additional hour. Excess sodium hydride was destroyed by the addition of water, and the mixture was diluted with ether and washed with water. The aqueous layer was extracted with ether (three times) and the combined extracts were dried (magnesium sulfate) and concentrated. The crude oily residue was flash chromatographed (silica gel/5-25% ethyl acetate:hexane) to obtain 1.67 g of the title compound as an oil.

Aufarbeitung

  1. temperaturecooled at 0°-5° C.
  2. additionwas added dropwise
  3. stirringstirring
  4. waitwas continued at this temperature for an additional hour
  5. customExcess sodium hydride was destroyed by the addition of water
  6. additionthe mixture was diluted with ether
  7. washwashed with water
  8. extractionThe aqueous layer was extracted with ether (three times)
  9. dry with materialthe combined extracts were dried (magnesium sulfate)
  10. concentrationconcentrated
  11. customchromatographed (silica gel/5-25% ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3fba0eea40214bbda207eea22a95b2cf
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04752645

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