Methylamine → N-[4-(3-Methylamino-1-propylthio)phenyl]methanesulfonamide Hydriodide

HRID 1030282Notes

Reaction equation

HRID 1030282 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][S: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>[IH:1].[CH3:22][NH:23][CH2:2][CH2:3][CH2:4][S: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

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 19822344N-[4-(3-Iodo-1-propylthio)phenyl]methanesulfonamide

Product 1

HCID 86745676N-[4-(3-Methylamino-1-propylthio)phenyl]methanesulfonamide HydriodideYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-[4-(3-iodo-1-propylthio)phenyl]methanesulfonamide (4.8 g, 0.13 mol), THF (28 mL), and 40 wt % methylamine in water (56 mL) was stirred at room temperature for 2 hours. The mixture was concentrated, taken up in 2:1 EtOH/toluene, and concentrated to give 4.9 g (94%) of product as a brown solid m.p. 80°-83° C.

Workup

  1. concentrationThe mixture was concentrated
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-44848985704642caa09ce32dec9af53c
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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