Methylamine → 4-[1-Hydroxy-2-(methylamino)ethyl]benzenesulfonamide

HRID 23674

Reaktionsgleichung

Reaktionsgleichung von HRID 23674
[CH3:1][NH2:2].[O:3]1[CH2:5][CH:4]1[C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1>CO>[OH:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:5][NH:2][CH3:1]

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 225742834-(Oxiran-2-yl)benzene-1-sulfonamide

Produkt 1

HCID 101927084-[1-Hydroxy-2-(methylamino)ethyl]benzenesulfonamideAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl amine (20 mL, 40 mmol, 2.0 M in methanol) was added 4-oxiran-2-ylbenzenesulfonamide (Preparation 49)(0.52 g, 2.6 mmol) at 0° C. The clear solution was warmed to room temperature and stirred overnight. The solvent and excess of methyl amine was evaporated to yield an oil. The crude oil was dissolved in methanol (5 mL), and stirred with resin (BioRad 50W×2, 1 g) for 4 hours. The resin was collected by filtration and washed with methanol (3×15 mL). The product on the resin was washed off with NH4OH/CH3OH (20 mL, 10% ammonium hydroxide aqueous solution (Aldrich, 29.4% NH3) in methanol). The solution was concentrated to dryness, and treated with high vacuum to give the title compound (0.19 g) as a white solid.

Aufarbeitung

  1. customThe solvent and excess of methyl amine was evaporated
  2. customto yield an oil
  3. filtrationThe resin was collected by filtration
  4. washwashed with methanol (3×15 mL)
  5. washThe product on the resin was washed off with NH4OH/CH3OH (20 mL, 10% ammonium hydroxide aqueous solution (Aldrich, 29.4% NH3) in methanol)
  6. concentrationThe solution was concentrated to dryness
  7. additiontreated with high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bfbe96447d564e3bb7f88344810de5d6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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