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

HRID 583330Notes

Reaction equation

HRID 583330 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl.O>[CH2:1]([NH:8][S:26]([C:23]1[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=1)(=[O:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 7504BenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 741351N-benzyl-4-methoxybenzenesulfonamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.358 g (0.05 mole) of benzylamine and 7.755 g (0.06 mole) of N,N-diisopropylethylamine in 80 mL of CH2Cl2 at room temperatue was added slowly 11.365 g (0.055 mole) of 4-methoxybenzenesulfonyl chloride. The resulting mixture was stirred for 18 hr at room temperature and diluted with water. The organic layer was separated, washed with NaHCO3, water, brine, dried over MgSO4, filtered and concentrated. The residue was boiled in CH2Cl2 :Hexane (1:4), cooled and filtered to provide 11.79 g (85%) of the desired product as a cream solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with NaHCO3, water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-62d6405be1624f8689428c6bfc4f9ac0
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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