Dichloromethane methanol → 4-Hydroxy-3-n-propylbenzenesulfonamide

HRID 865532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865532
[CH2:1]([C:4]1[CH:5]=[C:6]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[OH:10])[CH:2]=[CH2:3].[H][H].CO.C(Cl)Cl>C(O)C.[Pd]>[OH:10][C:9]1[CH:8]=[CH:7][C:6]([S:11]([NH2:14])(=[O:12])=[O:13])=[CH:5][C:4]=1[CH2:1][CH2:2][CH3:3]

Komponenten

6

Edukt 3

HCID 21226129Dichloromethane methanolHCID 217087083-Allyl-4-hydroxybenzenesulfonamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 190804514-Hydroxy-3-n-propylbenzenesulfonamideAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A Parr hydrogenation flask was charged with a solution of 3.04 g (14.30 mmol) of the product of Step A dissolved in 25 mL of ethanol and 0.300 g of a 10% palladium on carbon catalyst was added. The flask was mounted in the hydrogenation apparatus, freed of air, pressurized with hydrogen (40 psig) and shaken for 15 minutes. At the end of this period TLC analysis (3% MeOH-CH2Cl2, 2 elutions) indicated that the reaction was complete and the reaction mixture was filtered and evaporated. The product was dried in vacuo to afford 3.06 g (99%) of the title compound. 1H-NMR (400 MHz, CD3OD, ppm): δ 0.94 (t, J=7.20 Hz, 3H), 1.58-1.68 (m, 2H), 2.01-2.62 (m, 2H), 6.82 (d, J=8.40 Hz, 1H), 7.55 (dd, J=2.40, 8.40 Hz, 1H), 7.60 (d, J=2.40 Hz, 1H). FAB-MS m/e=216 (M+1).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. customevaporated
  3. customThe product was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-28e008a02e934ccea8a4bbb05539ff29
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565485

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