Methanesulfonyl chloride → N-(4-bromo-2-ethylphenyl)methanesulfonamide

HRID 2387063Notes

Reaction equation

HRID 2387063 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13]>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:12]([CH3:11])(=[O:14])=[O:13])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 28012834-Bromo-2-ethylaniline

Product 1

HCID 6469152N-(4-bromo-2-ethylphenyl)methanesulfonamideYield 81%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-2-ethyl-aniline (2 mL, 14 mmol) dissolved in anhydrous pyridine (35 mL) at room temperature was treated with methylsulfonyl chloride (1.3 mL, 16.8 mmol). The reaction was stirred at that temperature for 15 hours before it was diluted with EtOAc. The mixture was washed with H2O, brine and dried over MgSO4. The solvent was removed in vacuo and the residue was purified with flash chromatography (SiO2, 5-30% EtOAc in hexanes) to afford the desired product (3.1 g, 81% yield). 1H NMR (300 MHz, CDCl3): δ 1.25 (t, J=7.5 Hz, 3 H), 2.61-2.68 (m, 2 H), 3.02 (s, 3 H), 6.36 (s, 1 H), 7.36-7.39 (m, 3 H).

Workup

  1. washThe mixture was washed with H2O, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified with flash chromatography (SiO2, 5-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4be86484a1144518a2be9b9ab3fc2262
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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