p-Bromobenzenesulfonyl chloride → 4-bromo-N-(2-pyridin-2-ylethyl)benzenesulfonamide

HRID 2103623Notes

Reaction equation

HRID 2103623 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.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][NH2:20].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:20][CH2:19][CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 759192-PyridineethanamineHCID 516892Sodium Bicarbonate

Product 1

HCID 35270444-bromo-N-(2-pyridin-2-ylethyl)benzenesulfonamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add a solution of 4-bromo-benzenesulfonyl chloride (1.278 g, 5.0 mmol) in 10 mL dichloromethane at r.t. to a solution of 2-pyridin-2-yl-ethylamine (611 mg, 5.0 mmol) and triethylamine (708 μL, 5.0 mmol) in 5 mL dichloromethane over a period of 20 min via syringe pump and stir for 12 h. Add 20 mL saturated aqueous sodium bicarbonate solution and extract the aqueous phase with dichloromethane. Wash the combined organic extracts with brine, dry over sodium sulfate, filtrate and concentrate under reduced pressure to obtain 4-bromo-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide (1.67 g) as a pale yellow oil which slowly crystallizes upon storage at ambient temperature. Further purification is not necessary. MS (m/e): 342 (M+H).

Workup

  1. extractionextract the aqueous phase with dichloromethane
  2. washWash the combined organic extracts with brine
  3. dry with materialdry over sodium sulfate, filtrate
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-b2b1625b0c904ba4bb4cd2594d858549
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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