Ethanesulfonyl chloride → N-(2-bromophenyl)ethanesulfonamide

HRID 1523752Notes

Reaction equation

HRID 1523752 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:9]([S:11](Cl)(=[O:13])=[O:12])[CH3:10]>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][S:11]([CH2:9][CH3:10])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 119922-Bromoaniline

Product 1

HCID 3362983N-(2-bromophenyl)ethanesulfonamideYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 2-bromoaniline (344 mg, 2.0 mmol) in pyridine (5 mL) was slowly added ethyl-sulfonyl chloride (257 mg, 2.0 mmol) at rt and the mixture was stirred at rt for 16 hours. The pyridine was removed under reduced pressure and resulting residue diluted with water (30 mL) and extracted with DCM (10 mL×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by FCC to give the title compound (240 mg, 45%). MS (ESI): mass calcd. for C8H10BrNO2S 262.96 m/z found 264.1 [M+H]+. 1H NMR (300 MHz, CDCl3) δ 7.71 (dd, J=4.8, 1.5, 1H), 7.59 (dd, J=4.8, 1.5, 1H), 7.32-7.28 (m, 1H), 7.08-7.05 (m, 1H), 6.77 (bs, 1H), 3.14 (q, J=7.2, 2H), 1.41 (t, J=7.5, 3H).

Workup

  1. customat rt
  2. customThe pyridine was removed under reduced pressure
  3. customresulting residue
  4. extractionextracted with DCM (10 mL×2)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-c2989eec91ee48ef85a4aaf6316e5bb4
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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