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

HRID 23674

Reaction equation

HRID 23674 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 101927084-[1-Hydroxy-2-(methylamino)ethyl]benzenesulfonamideYield 31.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bfbe96447d564e3bb7f88344810de5d6
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

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