4-Acetylbenzenesulfonyl chloride → 4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide

HRID 1162477Notes

Reaction equation

HRID 1162477 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=[O:12])[CH3:11]>N1C=CC=CC=1>[C:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:9][C:4]2[C:5]([Cl:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 2664184-Acetylbenzenesulfonyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 595195144-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-chloropyridin-3-amine (1.535 g, 7.399 mmol, Asymchem Laboratories, Morrisville, N.C.) was dissolved in pyridine (20 mL), and 4-acetylbenzenesulfonyl chloride (2.436 g, 11.14 mmol) was added. The reaction flask was fit with a reflux condensor and placed in a preheated oil bath (110 C-115 C) and stirred under nitrogen for 2 hours. The reaction was then cooled to room temperature, concentrated, and poured into a biphasic solution of water (40 mL) and DCM (50 mL). The layers were separated, and the aqueous phase was extracted with DCM. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter plug (DCM to 20:1 DCM/MeOH) to afford 4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide. MS (ESI positive ion) m/z: 389 (M+1, 79Br), 391 (M+1, 81Br). Calcd. for C13H10BrClN2O3S: 388 (79Br), 390 (81Br).

Workup

  1. customplaced in a preheated oil bath
  2. concentrationconcentrated
  3. additionpoured into a biphasic solution of water (40 mL) and DCM (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with DCM
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on a silica gel
  10. filtrationfilter plug (DCM to 20:1 DCM/MeOH)

Sources & evidence

ORD record
ord-5fba60a57a8c4e8e9f17f8994174d6d6
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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