Reaction #1563890

ord-6f8ebbac375646b1b282f1ad582046b0

Reaction equation

COc1ccccc1NC(=O)c1c(N)cccc1Sc1ccc([N+](=O)[O-])cc1
Compound 25
COc1ccccc1NC(=O)c1c(N)cccc1Sc1ccc([N+](=O)[O-])cc1
2-amino-N-(2-methoxyphenyl)-6-(4-nitrophenylthi-o)benzamide
O=S(=O)(Cl)c1ccccc1
benzenesulfonyl chloride
COc1ccccc1NC(=O)c1c(NS(=O)(=O)c2ccccc2)cccc1Sc1ccc([N+](=O)[O-])cc1
N-(2-methoxyphenyl)-2-(4-nitrophenylthio)-6-(phenylsulfonamido)benzamide
Yield 67.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationthe reaction mixture was concentrated under reduced pressure
  2. 2
    Washwashed with water (3×20 mL)
  3. 3
    Dryingdried over anhydrous Na2SO4
  4. 4
    Filtrationfiltered
  5. 5
    Concentrationconcentrated under reduced pressure
  6. 6
    OtherThe residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)
  7. 7
    Otherto provide a white solid

Procedure

Compound 25 (1.0 equiv.) was dissolved in azabenzene (40 mL) at room temperature. To this mixture was added benzenesulfonyl chloride (1.2 equiv.). After being stirred for 10 Hours at room temperature, the reaction mixture was concentrated under reduced pressure. The crude residue was diluted ethyl acetate (50 mL), washed with water (3×20 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a white solid. 67% yield;

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09402819B2uspto-grants-2016_08