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

HRID 1393844Notes

Reaction equation

HRID 1393844 reaction equation
Cl.[CH2:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[CH2:2]([NH:9][S:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2724127Benzylammonium chloride

Product 1

HCID 741351N-benzyl-4-methoxybenzenesulfonamideYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Benzylamine hydrochloride (21.5 g, 150.0 mmol) was dissolved in chloroform (114 ml) and cooled to 0° C. Triethylamine (20.9 ml, 150.0 mmol) and 4-methoxybenzenesulfonyl chloride (10.3 g, 50.0 mmol) were added to the solution, and the mixture was reacted for 2 hours at room temperature, followed by for 1 hour at 60° C. After standing to cool, the reaction mixture was washed with 4N hydrochloric acid (200 ml×3), water (100 ml×2) and saturated brine (50 ml) successively. Then, the solvent was dried over sodium sulfate and evaporated out, to give N-benzyl-4-methoxybenzenesulfonamide (13.25 g, 96%).

Workup

  1. customthe mixture was reacted for 2 hours at room temperature
  2. customfollowed by for 1 hour at 60° C
  3. temperatureto cool
  4. washthe reaction mixture was washed with 4N hydrochloric acid (200 ml×3), water (100 ml×2) and saturated brine (50 ml) successively
  5. dry with materialThen, the solvent was dried over sodium sulfate
  6. customevaporated out

Sources & evidence

ORD record
ord-136ba12230a140b690da43615045e647
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

Loading…