Allyl bromide → N-allyl-N-(2-bromo-5-nitrophenyl)methanesulfonamide

HRID 618275Notes

Reaction equation

HRID 618275 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(CC)=O>[CH2:3]([N:15]([C:7]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=1[Br:5])[S:16]([CH3:19])(=[O:17])=[O:18])[CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 18789758N-(2-bromo-5-nitrophenyl)methanesulfonamide

Product 1

HCID 18789667N-allyl-N-(2-bromo-5-nitrophenyl)methanesulfonamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Allyl bromide (1.36 g, 11.25 mmol) was added to a mixture of N-(2-bromo-5-nitrophenyl)methanesulfonamide (1.66 g, 5.62 mmol) and cesium carbonate (5.49 g, 16.86 mmol) in methylethylketone (20 ml). The mixture was heated to reflux for 2 hr. The mixture was cooled and poured onto water. The product was extracted into ethyl acetate (2×75 ml) and the extracts were dried (anhydrous MgSO4) and concentrated to provide 1.88 g of N-allyl-N-(2-bromo-5-nitrophenyl)methanesulfonamide which required no purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hr
  3. temperatureThe mixture was cooled
  4. additionpoured onto water
  5. extractionThe product was extracted into ethyl acetate (2×75 ml)
  6. dry with materialthe extracts were dried (anhydrous MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d399b87b3b4a454f911de8126ce0853f
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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