Triethylamine → 4-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide

HRID 1644715

Reaktionsgleichung

Reaktionsgleichung von HRID 1644715
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21]([C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH:25]=[O:26])#[CH:22].C(OCC)(=O)C>C(#N)C.[Cu]I>[CH:25]([C:24]1[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=1[C:21]#[C:22][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1)=[O:26]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 128184-Bromo-N,N-dimethylbenzenesulphonamideHCID 6403682-Ethynylbenzaldehyde

Produkt 1

HCID 593508554-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-bromo-N,N-dimethylbenzenesulfonamide (610 mg, 2.31 mmol) bis(triphenylphosphine)palladium(II) chloride (Pd(PPh3)2Cl2) (33 mg, 0.05 mmol), copper (I) iodide (5 mg, 0.03 mmol) and triethylamine (3 mL) was degassed with argon. To the above mixture was added a degassed solution of 2-ethynyl-benzaldehyde (300 mg, 2.31 mmol) in acetonitrile (3 mL). The resulting mixture was heated at 80° C. for 3 hours under argon, and then cooled to room temperature, treated with ethyl acetate, and then washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 5-40% ethyl acetate in hexane) gave 4-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide (454 mg, 63%) as a brown oil. MS (ESI+) cald. for C17H15NO3S [(M+H)+] 313, obsd. 314.

Aufarbeitung

  1. customwas degassed with argon
  2. temperaturecooled to room temperature
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-29c8b36c6f7d4c1f91e31f412ae7f1f8
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124629B2

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