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

HRID 1686972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1686972
[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-133a83be2f7d444f8f6131698691fe13
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

Notizen zur Reaktion

Wird geladen…