4-Methoxybenzenesulfonyl chloride → N-benzyl-4-methoxybenzenesulfonamide

HRID 264311Notes

Reaction equation

HRID 264311 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(Cl)(Cl)Cl>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:19])=[O:18])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 7504Benzylamine

Product 1

HCID 741351N-benzyl-4-methoxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Benzylamine (16.0 mL, 145.2 mmol) is dissolved in chloroform (110 mL), and the solution is cooled to 0° C. To this solution is added 4-methoxybenzenesulfonyl chloride (10.0 g, 48.4 mmol). The reaction is stirred at room temperature for 1 hour, and then refluxed for 1 hour. After cooling back to room temperature, the reaction is washed three times with 4N hydrochloric acid (200 mL), twice with water (100 mL), once with brine (50 mL), then dried (Na2SO4), and the solvent is evaporated to give N-[4-methoxybenzenesulfonyl]-benzylamine.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureAfter cooling back to room temperature
  3. washthe reaction is washed three times with 4N hydrochloric acid (200 mL)
  4. dry with materialtwice with water (100 mL), once with brine (50 mL), then dried (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-480680a942d14e20afb3ab5e47cdfdb3
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

Loading…