Dimethylformamide → HCID 70873547, Verbindung

HRID 2172181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172181
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:37])([CH3:36])[CH2:23][CH2:24]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:38][C:39]1[NH:40][CH:41]=[C:42]([N+:44]([O-:46])=[O:45])[N:43]=1.C(=O)([O-])O.[Na+].CN(C)C=O>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:37])([CH3:36])[CH2:23][CH2:24][N:40]3[CH:41]=[C:42]([N+:44]([O-:46])=[O:45])[N:43]=[C:39]3[Cl:38])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 86709367HCID 86709367, VerbindungHCID 178526855HCID 178526855, Verbindung

Produkt 1

HCID 70873547HCID 70873547, VerbindungAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

4-{4-[2-Hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butoxy]phenyl}piperazine-1-carboxylic acid tert-butyl ester (4.69 g, 8.77 mmol), 2-chloro-4-nitro-1H-imidazole (1.55 g, 10.52 mmol), sodium hydrogen carbonate (0.88 g) and dimethylformamide (47 ml) were mixed, and the mixture was stirred at 90 to 100° C. overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. After filtering under reduced pressure, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→3:7) to afford the title compound as a yellow amorphous solid (2.12 g).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtering under reduced pressure
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→3:7)

Quellen und Nachweise

ORD-Eintrag
ord-978cd0bc9e684e958ff5e8b1894a115d
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051333B2

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