p-Bromobenzenesulfonyl chloride → 4-Bromo-N-(2-chloro-4-pyridinyl)benzenesulfonamide

HRID 2234976Notes

Reaction equation

HRID 2234976 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.[NH2:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1>N1C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 844322-Chloropyridin-4-amine

Product 1

HCID 589881394-Bromo-N-(2-chloro-4-pyridinyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

4-Bromobenzenesulfonyl chloride (3.19 g, 12.5 mmol) was added to a solution of 4-amino-2-chloropyridine (642 mg, 5 mmol) in pyridine (5 ml) and dichloromethane (5 ml). The reaction mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue suspended in 2M NaOH (25 ml) and heated at 60° C. for 1 h. The reaction mixture was extracted with ethyl acetate (2×25 ml). The extracts were washed, dried and evaporated. The residue was suspended in methanol and filtered. Evaporation of the filtrate and trituration with diethyl ether afforded the title compound (D3), 1H NMR (DMSO) δ: 6.54 (1H, d), 6.62 (1H, s), 7.60-7.63 (4H, m), 7.66 (1H, d).

Workup

  1. customThe solvent was evaporated
  2. temperatureheated at 60° C. for 1 h
  3. extractionThe reaction mixture was extracted with ethyl acetate (2×25 ml)
  4. washThe extracts were washed
  5. customdried
  6. customevaporated
  7. filtrationfiltered
  8. customEvaporation of the filtrate and trituration with diethyl ether

Sources & evidence

ORD record
ord-f3a3f9767cf64adc878290c65aae2ea7
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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