HCID 19605469, compound → HCID 19605490, compound

HRID 1603620Notes

Reaction equation

HRID 1603620 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]([N:17](C)[C:18](=O)C)[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>O1CCOCC1.[OH-].[Na+]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]([NH:17][CH3:18])[CH:14]=[CH:15][CH:16]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 19605469HCID 19605469, compound

Product 1

HCID 19605490HCID 19605490, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

1.19 g (0.0039 mol) of N-[3-(4-amino-benzenesulphonyl)-phenyl]-N-methyl-acetamide were dissolved in a mixture of 70 ml of dioxane and 70 ml of IN NaOH and heated at reflux for 5 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 1:1. The solvent was removed from the product-containing fractions and the residue was recrystallized from ethyl acetate/ether. There was obtained 0.63 g (62%) of [3-(4-amino-benzenesulphonyl) -phenyl]-methylamine as yellow crystals; m.p.: 125-126° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 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 1:1
  10. customThe solvent was removed from the product-containing fractions
  11. customthe residue was recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-d5d47618b91f47a2a1b2a13a3b76e444
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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