Potassium Iodide → HCID 71252434, Verbindung

HRID 2411390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2411390
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[C:4]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:3]=1.[CH2:28]([C@@H:30]1[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[NH:31]1)[CH3:29].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:31]3[C@H:30]([CH2:28][CH3:29])[CH2:34][CH2:33][S:32]3(=[O:36])=[O:35])=[CH:3][C:4]=2[S:24]([CH3:27])(=[O:26])=[O:25])=[O:9])[CH2:11][CH2:12]1

Komponenten

9

Edukt 5

HCID 4875Potassium IodideHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 58484856(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneHCID 86676750HCID 86676750, Verbindung

Produkt 1

HCID 71252434HCID 71252434, VerbindungAusbeute 8,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of (4-bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (451 mg) described in Preparation Example 110, (R)-3-ethylisothiazolidine 1,1-dioxide (150 mg) described in Preparation Example 3, potassium carbonate (276 mg), potassium iodide (332 mg) and copper(I) iodide (95 mg) were added toluene (3 mL) and N,N′-dimethylethylenediamine (110 μL), and the mixture was stirred with heating under reflux for 15 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (44 mg).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 15 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fbe31c5fccfa455e988085886a836619
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816079B2

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