HCID 53762093, compound → HCID 57120877, compound

HRID 1603617Notes

Reaction equation

HRID 1603617 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([N:17](C)[C:18](=O)C)[CH:13]=[C:14]([Br:16])[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCOCC1.[OH-].[Na+]>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([NH:17][CH3:18])[CH:13]=[C:14]([Br:16])[CH:15]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 53762093HCID 53762093, compound

Product 1

HCID 57120877HCID 57120877, compoundYield 958.7%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

0.10 g (0.000275 mol) of N-(3-benzenesulphonyl-5-bromophenyl)-N-methylacetamide was dissolved in a mixture of 5.5 ml of dioxane and 5.5 ml of 1N NaOH and heated at reflux for 1 hr. 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 and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:2. There was obtained 0.86 g (96%) of (3-benzenesulphonyl-5-bromophenyl)-methylamine as a pale yellow solid; m.p.: 143-145° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  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. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:2

Sources & evidence

ORD record
ord-3d9a8a4246ab4880869ab2e6b47684be
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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