Methylamine → N-Methyl-4-nitrobenzenesulfonamide

HRID 1584235Notes

Reaction equation

HRID 1584235 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][NH2:15]>CCOCC>[CH3:14][NH:15][S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 232993N-Methyl-4-nitrobenzenesulfonamideYield 98.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 4-nitrobenzenesulfonyl chloride (5 g, 22.56 mmol) in ether (250 ml), methylamine (5 ml, 40% aq. solution, 56.4 mmol) was added, and the mixture was stirred at room temperature. After 16 hr, the reaction mixture was concentrated to remove the solvent and the residue was resuspended in methylene chloride. After washing with 2N HCl and brine, the organic fractions were dried (MgSO4), filtered and concentrated to give N-methyl-4-nitrobenzenesulfonamide (4.8 g, 98%): mp (DSC) 109° C. Anal Calc'd. for C7H8N2O4S: C, 38.89; H, 3.73; N, 12.96. Found: C, 38.83; H, 3.72; N, 12.96.

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated
  3. customto remove the solvent
  4. washAfter washing with 2N HCl and brine
  5. dry with materialthe organic fractions were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-520c88aa7cd541a8ae8c87c2923d0b13
Source dataset
uspto-grants-1999_08
Patent number
US05932598

Reaction notes

Loading…