Methylamine → N-Methyl-4-nitrobenzenesulfonamide

HRID 2304589Notes

Reaction equation

HRID 2304589 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-8b38165029fb428fb83862b60290943d
Source dataset
uspto-grants-2002_08
Patent number
US06436967B1

Reaction notes

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