Water → HCID 12277508, Verbindung

HRID 1891038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891038
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[CH2:4][C:3]1=[O:13].Br[CH2:15][CH2:16]Br.C([O-])([O-])=O.[K+].[K+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.CN(C)C=O>[CH3:1][N:2]1[C:3](=[O:13])[C:4]2([CH2:16][CH2:15]2)[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 3494362-Methylisoquinoline-1,3(2H,4H)-dione

Produkt 1

HCID 12277508HCID 12277508, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of N-methylhomophthalimide (4.05 kg), 1,2-dibromoethane (2.39 L), and Bu4NHSO4 (785 g) in N,N-dimethylformamide (32 L) were added K2CO3 (6.39 kg) and N,N-dimethylformamide (8.5 L) at room temperature. Then the solution was heated to 70° C., and was stirred for 2 hours at 68˜70° C. After cooling the reaction mixture to 40° C., water (81 L) was added. After the slurry was stirred for 1 hour at 40° C., it was allowed to cool to room temperature and was stirred overnight. The suspension was filtered, and the obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L), twice, and water (20 L), sequentially. It was dried at room temperature under N2 flow for several hours and then under the reduced pressure overnight to afford the title compound as pale pink crystal (4.67 kg, 4.30 kg assay, 92% yield).

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture to 40° C.
  2. stirringAfter the slurry was stirred for 1 hour at 40° C.
  3. temperatureto cool to room temperature
  4. stirringwas stirred overnight
  5. filtrationThe suspension was filtered
  6. washthe obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L)
  7. customIt was dried at room temperature under N2 flow for several hours

Quellen und Nachweise

ORD-Eintrag
ord-7a0c645d69034a378ae9cc0eba811ae2
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507504B2

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