Acetone → 1-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 69042

Reaktionsgleichung

Reaktionsgleichung von HRID 69042
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:23]=[CH:22][C:9]2[N:10]([CH2:20][CH3:21])[C:11](=[O:19])[C:12]([CH3:18])([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:8]=2[CH:7]=1.[I-:24].[Na+].CC(C)=O>O>[CH2:20]([N:10]1[C:11](=[O:19])[C:12]([CH3:18])([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:8]2[CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][I:24])[CH:23]=[CH:22][C:9]1=2)[CH3:21]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 686732537-(3-Chloropropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Produkt 1

HCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

7-(3-Chloropropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione (2.18 g) and sodium iodide (4.8 g) were added to acetone (50 ml), and heated under reflux for 8.5 hours. The reaction mixture was cooled to room temperature, water was added, and extraction with ethyl acetate was performed. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated under reduced pressure to give the title compound (2.76 g) as a colorless oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 8.5 hours
  3. extractionextraction with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
  7. concentrationThe purified product was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-59dd04d6f65c49a195f1d8fc186758b4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822453B2

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