Triphenylphosphine → 2-(Prop-1-yn-1-yl)benzene-1-sulfonamide

HRID 1981844

Reaktionsgleichung

Reaktionsgleichung von HRID 1981844
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].P(C1C=CC=CC=1)(C1C=CC=CC=1)[C:13]1[CH:18]=CC=C[CH:14]=1.CC(C(OC1C=CC(C(O)CNC)=CC=1OC(C(C)(C)C)=O)=O)(C)C.Cl>CN(C)C=O.C(N(CC)CC)C.Cl[Pd]Cl.[Cu]I>[C:14]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9])#[C:13][CH3:18]

Komponenten

8

Edukt 3

HCID 11776TriphenylphosphineHCID 71486Dipivefrin HydrochlorideHCID 28248922-Iodobenzene-1-sulfonamide

Produkt 1

HCID 197936102-(Prop-1-yn-1-yl)benzene-1-sulfonamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24290Palladium ChlorideKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 28.3 g (0.1 mole) of 2-iodophenylsulfonamide in 350 ml of dimethylformamide and 100 ml of triethylamine are added 1.0 g of palladium dichloro-bis(triphenylphosphite) complex, PdCl2 [P(C6H5)3 ]2, and 0.5 g of copper(I) iodide (CuI). Gaseous propine is then introduced into this solution until the starting material is completely reacted. The reaction mixture is filtered and the residue is concentrated in vacuo and then taken up in water. The precipitate is isolated and dried. Recrystallisation from ethyl acetate/hexane yields 15.6 g (80%) of 2-(propyn-1-yl)phenylsulfonamide with a melting point of 147°-149° C.

Aufarbeitung

  1. customis completely reacted
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe residue is concentrated in vacuo
  4. customThe precipitate is isolated
  5. customdried
  6. customRecrystallisation from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-580b3810031b4a3cb32ee896c1a1b03f
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04594097

Verknüpfte Notizen

Wird geladen…