Water → HCID 11232442, Verbindung

HRID 1590620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590620
Cl[C:2]1[N:7]=[N:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O.[Cu]I>[C:24]1([C:30]#[C:31][C:2]2[N:7]=[N:6][C:5]([S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 19009006HCID 19009006, Verbindung

Produkt 1

HCID 11232442HCID 11232442, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 6-chloro-3-phenylsulfonylpyridazine (8.4 g) bis(triphenylphosphine)palladium(II) chloride (98%; 0.24 g), copper(I) iodide (95%; 63 mg), and triethylamine (9.2 ml) in N,N-dimethylformamide (84 ml) was added phenylacetylene (4.7 ml), and the mixture was stirred for 0.5 hour at 80° C. After being cooled to room temperature, water (168 ml) was added to the reaction mixture. The precipitate formed was collected, washed with water, and dried. Recrystallization of the crude product from a mixture of diisopropyl ether and acetone (2:1) gave 6-(2-phenylethynyl)-3-phenylsulfonylpyridazine (5.5 g). After the mother liquor was concentrated in vacuo, the residue was triturated with acetone. The precipitate was collected and dried to give a second crop of the pure material (2.0 g).

Aufarbeitung

  1. temperatureAfter being cooled to room temperature
  2. customThe precipitate formed
  3. customwas collected
  4. washwashed with water
  5. customdried
  6. customRecrystallization of the crude product
  7. additionfrom a mixture of diisopropyl ether and acetone (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-41cff87a10c04e47a151e1dd5a5c729b
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204346

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