N-[3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-N-methylacetamide → [3-Bromo-5-(4-nitrophenylsulphanyl)-phenyl]-methylamine

HRID 1603625Notes

Reaction equation

HRID 1603625 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:18](C)[C:19](=O)C)[CH:5]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:7]=1>O1CCOCC1.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([NH:18][CH3:19])[CH:5]=[C:6]([S:8][C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 19605546N-[3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-N-methylacetamide

Product 1

HCID 19605547[3-Bromo-5-(4-nitrophenylsulphanyl)-phenyl]-methylamineYield 106.6%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

0.79 g (0.002 mol) of N-[3-bromo-5-(4-nitrophenylsulphanyl) -phenyl]-N-methylacetamide was dissolved in a mixture of 10 ml of dioxane and 10 ml of 1N NaOH and heated at reflux for 2 hrs. Subsequently, the organic solvent was distilled off and the residue was made neutral with 1N HCl and extracted with ethyl acetate. The organic phase was washed with water and sat. sodium chloride solution, dried over MgSO4, filtered, concentrated and dried. There was obtained 0.723 g (100%) of [3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-methylamine as red crystals; m.p.: 96-98° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hrs
  3. distillationSubsequently, the organic solvent was distilled off
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and sat. sodium chloride solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

Sources & evidence

ORD record
ord-e0a6a9633f824d9796c9d9e18ec9292c
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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