HCID 19605536, compound → HCID 19605467, compound

HRID 1603624Notes

Reaction equation

HRID 1603624 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:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=1>O1CCOCC1.[OH-].[Na+]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:5]=[C:4]([NH:18][CH3:19])[CH:3]=[C:2]([Br:1])[CH:7]=2)(=[O:9])=[O:10])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 19605536HCID 19605536, compound

Product 1

HCID 19605467HCID 19605467, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

0.021 g (0.000054 mol) of N-[3-bromo-5-(4-aminobenzenesulphonyl)-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 and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:2. There was obtained 0.01 g (54%) of [3-(4-aminobenzenesulphonyl)-5-bromophenyl]-methylamine as yellow crystals. MS (ISP): me/e=343, 341 (C13H14BrN2O2S+).

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. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:2

Sources & evidence

ORD record
ord-4a74772e52f044fe806a8a1b18c36c94
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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