1,2-Dibromoethane → N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamide

HRID 2190181Notes

Reaction equation

HRID 2190181 reaction equation
[CH2:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH:2]=[CH2:3].[Br:17][CH2:18][CH2:19]Br>CN(C=O)C>[CH2:1]([N:4]([CH2:19][CH2:18][Br:17])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 78391,2-DibromoethaneHCID 22739612-nitro-N-prop-2-enylbenzenesulfonamide

Product 1

HCID 58052488N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamideYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Allyl-2-nitro-benzenesulfonamide (570 mg, 2.35 mmol) is dissolved in DMF (5 mL) and then CsCO3 (920 mg, 2.82 mmol) and 1,2-dibromoethane (884 mg, 4.71 mmol) is added. The mixture is then microwaved for 30 min at 150° C., then filtered and the solid washed with EtOAc (30 mL). The organic is washed with Brine (20 mL) and then dried over Na2SO4 and then concentrated to dryness. HPLC (CH3CN/H2O/0.1% TFA) provides N-Allyl-N-(2-bromo-ethyl)-2-nitro-benzenesulfonamide (400 mg, 48%). MS-ES [M+H]+=351.1.

Workup

  1. customThe mixture is then microwaved for 30 min at 150° C.
  2. filtrationfiltered
  3. washthe solid washed with EtOAc (30 mL)
  4. washThe organic is washed with Brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7ca97fd2748247cd82fe1002006e0123
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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