Methylamine → N-Methyl-4-nitrobenzenesulfonamide

HRID 29047Notes

Reaction equation

HRID 29047 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-ccb6d66ead81471897de02c5abc5b139
Source dataset
uspto-grants-2008_09
Patent number
US07420061B2

Reaction notes

Loading…