Benzenesulfonyl chloride → N-(5-bromopyridin-3-yl)benzenesulfonamide

HRID 1182936Notes

Reaction equation

HRID 1182936 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 57843412N-(5-bromopyridin-3-yl)benzenesulfonamideYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-bromopyridin-3-amine (1.00 g, 5.78 mmol) in pyridine (3.00 mL) was added benzenesulfonyl chloride (0.75 mL, 5.78 mmol) dropwise at 0° C. The mixture was stirred for 40 min at room temperature. The resulting solid was filtered, washed with water, and dried under vacuum to give N-(5-bromopyridin-3-yl)benzenesulfonamide (1.39 g, 77%) as a brown solid. 1H-NMR (DMSO-d6, Varian 400 MHz) δ 7.58-7.68 (4H, m), 7.79-7.81 (2H, m), 8.27 (1H, d, J=2.4 Hz), 8.37 (1H, d, J=2.0 Hz), 10.91 (1H, brs).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4a3baf818344481a9b261f78d520c04e
Source dataset
uspto-grants-2014_03
Patent number
US08664230B2

Reaction notes

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