Pyridine → 4-Bromobenzenesulfonamide

HRID 1370670Notes

Reaction equation

HRID 1370670 reaction equation
[N:1]1C=CC=CC=1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(Cl)Cl>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH2:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 696964-Bromobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The optically pure resin-bound secondary amine resin (from Step C) was swelled in DCM (200 mL). To the suspension was added pyridine (3.19 g) and then 4-bromophenylsulfonyl chloride (5.1 g, 20.0 millimole). The suspension was shaken overnight. The resin was filtered and washed with 3 portions of DCM, 3 portions of methanol, 3 portions of DCM, and 3 portions of methanol. The resin was dried in vacuo overnight.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with 3 portions of DCM, 3 portions of methanol, 3 portions of DCM, and 3 portions of methanol
  3. customThe resin was dried in vacuo overnight

Sources & evidence

ORD record
ord-244266272f3c4e4aba1d63ac07c87fc4
Source dataset
uspto-grants-2003_06
Patent number
US06583179B2

Reaction notes

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