Methylamine → N-Methyl-o-toluenesulfonamide

HRID 1262813Notes

Reaction equation

HRID 1262813 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[CH3:12][NH2:13]>C(Cl)Cl>[CH3:12][NH:13][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 8623o-Toluenesulfonyl chloride

Product 1

HCID 10197977N-Methyl-o-toluenesulfonamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylbenzenesulfonyl chloride (37.4 g, 0.196 mol) in methylene chloride (300 ml) at -5° to 0° under nitrogen was added liquid methylamine (27.5 ml, 0.588 mol) at a rate to maintain an internal temperature less than 10°. The reaction mixture was stirred at 0° for 1/2 hour and then allowed to warm to room temperature. After 11/4 hours, filtration and concentration of the filtrate gave an oil which solidified upon cooling. Washing the solid with n-butyl chloride gave N,2-dimethylbenzenesulfonamide as a light yellow powder (28.4 g, 78%), mp. 62°-64°.

Workup

  1. temperatureto maintain an internal temperature less than 10°
  2. filtrationAfter 11/4 hours, filtration and concentration of the filtrate
  3. customgave an oil which
  4. temperatureupon cooling
  5. washWashing the solid with n-butyl chloride

Sources & evidence

ORD record
ord-7c10f760bd43447a864f33b5e4e39c09
Source dataset
uspto-grants-1984_06
Patent number
US04454135

Reaction notes

Loading…