Triethylamine → N-methyl-1-(p-tolyl)methanesulfonamide

HRID 256603

Reaction equation

HRID 256603 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5](NC)=[CH:4][CH:3]=1.C([N:12]([CH2:15]C)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:15][NH:12][S:18]([CH2:17][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:9][CH:8]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12165Benzenamine, N,4-dimethyl-HCID 31297Methanesulfonyl chloride

Product 1

HCID 19917625N-methyl-1-(p-tolyl)methanesulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of p-methyl-N-methylaniline (5.00 g) and triethylamine (5.05 g) in dichloromethane (140 ml) was cooled to 0° C. and methanesulphonyl chloride (4.73 g) was added dropwise. The reaction mixture was stirred at ambient temperature for 2 hours and quenched with water (100 ml). The organic phase was washed with 2N aqueous hydrochloric acid solution (75 ml) and 2N aqueous sodium hydroxide solution (75 ml), dried (MGSO ) and the solvent removed by evaporation. Thus was obtained N-methyl-(4-tolyl)methanesulphonamide (5.3 g, 65%), m.p. 49°-52° C.

Workup

  1. customquenched with water (100 ml)
  2. washThe organic phase was washed with 2N aqueous hydrochloric acid solution (75 ml) and 2N aqueous sodium hydroxide solution (75 ml)
  3. customdried (MGSO )
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-374bc0fb75fa4517850d80a77b7aa4da
Source dataset
uspto-grants-1993_11
Patent number
US05258399

Linked notes

Loading…