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Dimethylformamide → 7-(3-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1183084
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Reaktionsgleichung

Reaktionsgleichung von HRID 1183084
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].CN(C=O)C.[CH2:27]([N:29]1[C:35](=[O:36])[C:34]([CH3:38])([CH3:37])[C:33](=[O:39])[N:32]([CH3:40])[C:31]2[CH:41]=[C:42]([OH:45])[CH:43]=[CH:44][C:30]1=2)[CH3:28]>C(OCC)(=O)C.O>[O:21]=[C:12]1[C:13]2[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:16])[N:11]1[CH2:10][CH2:9][CH2:8][O:45][C:42]1[CH:43]=[CH:44][C:30]2[N:29]([CH2:27][CH3:28])[C:35](=[O:36])[C:34]([CH3:37])([CH3:38])[C:33](=[O:39])[N:32]([CH3:40])[C:31]=2[CH:41]=1
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Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 686733851-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Produkt 1

HCID 686733627-(3-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione
Ausbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium carbonate (2.99 g, 21.6 mmol) and N-(3-bromopropyl)phthalimide (2.32 g, 8.65 mmol) were added to a DMF solution (50 ml) of 1-ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (1.89 g, 7.2 mmol), and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution, in this order. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→3:7). The purified product was concentrated to dryness under reduced pressure to thereby obtain 2.70 g (yield: 83%) of 7-(3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a white powder.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→3:7)
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bfebe6aaafef4a8388cc54f000ba1816
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08664217B2

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