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

HRID 2254662Notes

Reaction equation

HRID 2254662 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 (MgSO4) 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. dry with materialdried (MgSO4)
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-0d7d6b961b69478d9aa3095cb229d36a
Source dataset
uspto-grants-1993_08
Patent number
US05236948

Reaction notes

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