1-Butyne → 2-(But-1-yn-1-yl)-benzenesulfonamide

HRID 6380

Reaktionsgleichung

Reaktionsgleichung von HRID 6380
C(N(CC)CC)C.I[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16].[CH:19]#[C:20][CH2:21][CH3:22]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[C:19]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16])#[C:20][CH2:21][CH3:22]

Komponenten

7

Edukt 3

HCID 78461-ButyneHCID 8471TriethylamineHCID 28248922-Iodobenzene-1-sulfonamide2×

Produkt 1

HCID 197935882-(But-1-yn-1-yl)-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.1 g of bis(triphenylphosphine)palladium(II) chloride, 0.05 g of copper iodide and 18.5 ml of triethylamine are added to a solution of 5 g of 2-iodobenzenesulfonamide in 70 ml of N,N-dimethylformamide. At room temperature, argon and 1-butyne are slowly introduced. After 18 hours the thin-layer chromatogram no longer shows any 2-iodobenzenesulfonamide. The dimethylformamide is evaporated off at 0.1 torr and 40°, and the residue is chromatographed on 300 g of silica gel (Merck ST 60, 40-63 μm). Methylene chloride is used as eluant. In that manner, after concentration of the product-containing fractions at 15 torr and 40°, white pulverulent 2-(but-1-yn-1-yl)-benzenesulfonamide is obtained: 1H-NMR (300 MHz, CDCl3): 8.0 (d, d, 1H); 7.35 (d, d, 1H); 7.29 (d, t, 1H); 7.23 (d, t, 1H); 5.13 (s, 2H); 2.32 (q, 2H); 1.18 (t, 3H).

Aufarbeitung

  1. customThe dimethylformamide is evaporated off at 0.1 torr and 40°
  2. customthe residue is chromatographed on 300 g of silica gel (Merck ST 60, 40-63 μm)

Quellen und Nachweise

ORD-Eintrag
ord-c34b896f8df643aab6bb098bc5e91b2c
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248693

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