Dimethylformamide → 1,3-Diethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

HRID 1040664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040664
[H-].[Na+].CN(C=O)C.[CH2:8]([CH:10]1[C:16]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][NH:12][C:11]1=[O:23])[CH3:9].I[CH2:25][CH3:26]>O>[CH2:8]([CH:10]1[C:16]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][N:12]([CH2:25][CH3:26])[C:11]1=[O:23])[CH3:9]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 672635691-Ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

Produkt 1

HCID 672637981,3-Diethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Charge NaH (60% dispersion in mineral oil) to 100 ml RBF and wash with hexanes. Charge 10 ml anhydrous DMF and 1-Ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (0.500 g, 2.28 mmol). Stir 10 minutes at room temperature and then charge iodoethane (900 uL, 10 mmol) dropwise with syringe. Allow to stir overnight. Pour reaction into 75 ml water and extract with 3×30 ml EtOAc. Dry combined organic over MgSO4, filter and evaporated to yield 1,3-Diethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one. The crude product was used in the next step.

Aufarbeitung

  1. washwash with hexanes
  2. stirringto stir overnight
  3. additionPour
  4. extractionextract with 3×30 ml EtOAc
  5. customDry
  6. filtrationfilter
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4baae7d22bd241a9971a83ea9dd803ef
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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