Methylamine → N-methyl-2-nitrobenzene-1-sulfonamide

HRID 595959Notes

Reaction equation

HRID 595959 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH3:14][NH2:15].O1CCCC1>C(Cl)Cl>[CH3:14][NH:15][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 264906N-methyl-2-nitrobenzene-1-sulfonamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-nitrobenzene-1-sulfonyl chloride (4 g, 18.05 mmol) in DCM (60.2 mL) was cooled down to 0° C. with an ice water bath. TEA (7.55 mL, 54.1 mmol) and 2 M methylamine in tetrahydofuran (13.54 mL, 27.1 mmol) were added. The resulting solution was stirred at room temperature for 6 h. The reaction mixture was diluted with DCM, washed with sat. NaHCO3 (2×100 mL), brine (100 mL) and then dried over magnesium sulphate. The solution was filtered before concentrating under reduced pressure, and triturated in ether to afford N-methyl-2-nitrobenzenesulfonamide (3.12 g, 14.44 mmol, 80% yield). LCMS (m/z): 217.1 (MH+), 0.53 min.

Workup

  1. washwashed with sat. NaHCO3 (2×100 mL), brine (100 mL)
  2. dry with materialdried over magnesium sulphate
  3. filtrationThe solution was filtered
  4. concentrationbefore concentrating under reduced pressure
  5. customtriturated in ether

Sources & evidence

ORD record
ord-b62cf134dbf04b6abe17dae19c27954a
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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