Lithium Bromide → N-(2-Bromoethyl)-N-[2-(4-cyanophenoxy)ethyl]methanesulfonamide

HRID 899122Notes

Reaction equation

HRID 899122 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([O:7][CH2:8][CH2:9][N:10]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:11][CH2:12]OS(C)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[Br-:24].[Li+]>CC(C)=O>[Br:24][CH2:12][CH2:11][N:10]([CH2:9][CH2:8][O:7][C:6]1[CH:22]=[CH:23][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[S:18]([CH3:21])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 86616241Methanesulfonic acid 2-{[2-(4-cyanophenoxy)ethyl]methanesulfonylamino}ethyl ester

Product 1

HCID 69075823N-(2-Bromoethyl)-N-[2-(4-cyanophenoxy)ethyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methanesulfonic acid 2-{[2-(4-cyanophenoxy)ethyl]-methanesulfonylamino}ethyl ester (10 g, 0.028 mol; see step (iii) above) in dry acetone (100 mL), was added lithium bromide (4.8 g, 0.055 mol). The reaction mixture was added refluxed overnight under a nitrogen atmosphere, before being filtered and concentrated to give the title compound. Yield: 10 g (97%).

Workup

  1. additionThe reaction mixture was added
  2. temperaturerefluxed overnight under a nitrogen atmosphere
  3. filtrationbefore being filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-34a6591cfe56468ba7e3757dc14c94c1
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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