p-Bromobenzenesulfonyl chloride → N-Benzyl-4-bromobenzenesulfonamide

HRID 36493Notes

Reaction equation

HRID 36493 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 7504Benzylamine

Product 1

HCID 571651N-Benzyl-4-bromobenzenesulfonamideYield 57.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Bromobenzenesulfonyl chloride (14.05 g, 55 mmol) was added to a stirred solution of benzylamine (5.36 g, 50 mmol) and pyridine (400 ml) under nitrogen at room temperature. The resulting reaction mixture was stirred for 1 hr; then it was poured onto ice/water (800 ml) to form a yellow precipitate which was filtered and recrystallized from EtOH/water to give 9.44 g (53%) of the title compound as off-white needles, mp 116°-117° C.

Workup

  1. customThe resulting reaction mixture
  2. additionthen it was poured onto ice/water (800 ml)
  3. customto form a yellow precipitate which
  4. filtrationwas filtered
  5. customrecrystallized from EtOH/water

Sources & evidence

ORD record
ord-3b203ffad0524e8a81568be747831d0e
Source dataset
uspto-grants-1995_05
Patent number
US05414132

Reaction notes

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