N,N'-Dimethylethylenediamine → HCID 71252824, Verbindung

HRID 2411136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2411136
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][CH:14]1[CH2:18][S:17](=[O:20])(=[O:19])[NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:13][CH:14]1[CH2:18][S:17](=[O:20])(=[O:19])[N:16]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:15]1

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 59155177ZJNXUAJQNBXKSL-UHFFFAOYSA-N

Produkt 1

HCID 71252824HCID 71252824, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

To a mixture of ethyl 4-iodobenzoate (571 mg), 4-methylisothiazolidine 1,1-dioxide (280 mg) described in Preparation Example 9, potassium carbonate (572 mg) and copper(I) iodide (197 mg) were added toluene (6 mL) and N,N′-dimethylethylenediamine (230 μL), and the mixture was stirred with heating under reflux for 9 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 ethyl 4-(4-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoate. The obtained ethyl 4-(4-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoate was dissolved in tetrahydrofuran (5 mL), 1N aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated from the reaction mixture, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. To the obtained residue was added diethyl ether, and the precipitate was collected by filtration to give the title compound (210 mg).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 9 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-ca2f7ed5490f41d7a1d45a6d14c462bc
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816079B2

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