Methylamine → N-methyl-1-(3-nitrophenyl)methanesulfonamide

HRID 1941915Notes

Reaction equation

HRID 1941915 reaction equation
[CH3:1][NH2:2].[N+:3]([C:6]1[CH:7]=[C:8]([CH2:12][S:13](Cl)(=[O:15])=[O:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]>C1C=CC=CC=1>[N+:3]([C:6]1[CH:7]=[C:8]([CH2:12][S:13]([NH:2][CH3:1])(=[O:15])=[O:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13196775(3-Nitrophenyl)methanesulfonyl chloride

Product 1

HCID 13286046N-methyl-1-(3-nitrophenyl)methanesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

40% aqueous methylamine (10 mL, 0.1 mol) was added to a vigorously stirred solution of (3-nitrophenyl)methanesulfonyl chloride (2.36 g, 10 mmol) in benzene (30 mL) and allowed to stir for 2 h at room temperature. The benzene layer was separated, and the aqueous layer extracted with CH2Cl2 (2×25 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (30 mL), water (30 mL), filtered over anhydrous Na2SO4, filtered and the solvent removed under reduced pressure to give 2.07 g (90%) of (3-nitrophenyl)-N-methylmethanesulfonamide as crystals.

Workup

  1. customThe benzene layer was separated
  2. extractionthe aqueous layer extracted with CH2Cl2 (2×25 mL)
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 (30 mL), water (30 mL)
  4. filtrationfiltered over anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c854b0b7c3654929b69bc4429e777ffa
Source dataset
uspto-grants-2013_03
Patent number
US08389521B2

Reaction notes

Loading…