Water → N-[4-(3-Methylamino-1-propyloxy)phenyl]methanesulfonamide Hydriodide

HRID 1030277Notes

Reaction equation

HRID 1030277 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1.C1COCC1.[CH3:22][NH2:23].O>CCO.C1(C)C=CC=CC=1>[IH:1].[CH3:22][NH:23][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 19822359N-[4-(3-Iodo-1-propyloxy)phenyl]methanesulfonamide

Product 1

HCID 86745675N-[4-(3-Methylamino-1-propyloxy)phenyl]methanesulfonamide HydriodideYield 99%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

A mixture of N-[4-(3-iodo-1-propyloxy)phenyl]methanesulfonamide (1.32 g, 3.72 mmol), THF (8 mL), and 40 wt % methylamine in water (16 mL, 0.186 mol) was stirred at room temperature for 2 hours. The mixture was concentrated to give a brown oil, taken up in 2:1 EtOH/toluene, and concentrated to give 1.42 g (99%) of product as a pink solid m.p. 104°-107° C.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a brown oil
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-75f7942b48c343ed9a0a8babc2f38da3
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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