Sodium Hydroxide → N-[3-(dimethylamino)phenyl]methanesulphonamide

HRID 244524

Reaction equation

HRID 244524 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][N:7]([CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1.[OH-].[Na+]>O>[CH3:6][N:7]([CH3:15])[C:8]1[CH:9]=[C:10]([NH:14][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 76084N,N-dimethyl-m-phenylenediamine

Product 1

HCID 13796402N-[3-(dimethylamino)phenyl]methanesulphonamideYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulphonyl chloride (838 mg, 7.35 mmol) was added slowly to a cooled solution (5° C.) of N,N-dimethyl-1,3-phenylenediamine (1.00 g, 7.35 mmol) and sodium hydroxide (5M, 1.5 cm3) in water (10 cm3). The reaction was allowed to warm to room temperature overnight. The mixture was extracted with chloroform (3×15 cm3). The combined extracts were dried over sodium sulphate, filtered and the solvent removed under reduced pressure. Column chromatography (1:20 methanol/dichloromethane) gave the target material as a brown oil (1.24 g, 79%).

Workup

  1. extractionThe mixture was extracted with chloroform (3×15 cm3)
  2. dry with materialThe combined extracts were dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b8fd1201b5654d798122c4747976812a
Source dataset
uspto-grants-2014_02
Patent number
US08658665B2

Linked notes

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