Benzenesulfonyl chloride → N-[2-(3-bromophenyl)ethyl]benzenesulfonamide

HRID 2423526Notes

Reaction equation

HRID 2423526 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][NH2:20])[CH:15]=[CH:16][CH:17]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Br:11][C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][NH:20][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 70217363-Bromophenethylamine

Product 1

HCID 59321588N-[2-(3-bromophenyl)ethyl]benzenesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (1.54 mL, 12.00 mmol) was added to [2-(3-bromophenyl)ethyl]amine (2.00 g, 10.00 mmol) and N,N-di-iso-propylethylamine (5.22 mL, 29.99 mmol) in dichloromethane (33 mL) at 0° C. under argon and the reaction was allowed to warm to room temperature and stirred for 16 hours. The dichloromethane was concentrated under vacuum; diethyl ether was then added, followed by 10% citric acid. The solution was extracted with diethyl ether and the organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to give 3.22 g (95%) of N-[2-(3-bromophenyl)ethyl]benzenesulfonamide as a solid. 1H NMR (400 MHz, d6-DMSO): δ 7.77-7.73 (m, 2H), 7.70 (t, J=6 Hz, 1H), 7.62 (d, J=7 Hz, 1H), 7.57 (t, J=8 Hz, 2H), 7.40-7.34 (m, 2H), 7.22 (t, J=8 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 2.96 (q, J=7 Hz, 2H), 2.67 (t, J=7 Hz, 2H). ESI-LCMS m/z 340 (M+H)+.

Workup

  1. concentrationThe dichloromethane was concentrated under vacuum
  2. additiondiethyl ether was then added
  3. extractionThe solution was extracted with diethyl ether
  4. washthe organic layer was washed with saturated sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-8680c8e6c44e4142a592323f6a54c30b
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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