Methylamine → 4-bromo-N-methylbenzene-1-sulfonamide

HRID 881127Notes

Reaction equation

HRID 881127 reaction equation
C([O-])(O)=O.[Na+].[CH3:6][NH2:7].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:7][CH3:6])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 1012154-bromo-N-methylbenzene-1-sulfonamideYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a mixture of sat aq. NaHCO3 (42 g, 0.5 mol), CH2Cl2 (400 mL) and methylamine (51.7 g, 0.5 mol, 30% in methanol) was added a solution of 4-bromo-benzenesulfonyl chloride (127 g, 0.5 mol) in CH2Cl2 (100 mL). The reaction was stirred at 20° C. overnight. The organic phase was separated and dried over Na2SO4. Evaporation of the solvent under reduced pressure provided the 4-bromo-N-methyl-benzenesulfonamide (121 g, crude), which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ 7.64-7.74 (m, 4 H), 4.62-4.78 (m, 1 H), 2.65 (d, J=5.4 Hz, 3 H).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-20d1550d457442d1b1a49ae02e83e4c6
Source dataset
uspto-grants-2015_03
Patent number
US08993600B2

Reaction notes

Loading…