تفاعل #1563889

ord-68ff612d1b96417d9b4870621bb3ef95

معادلة التفاعل

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
OO
H2O2
COc1ccccc1NC(=O)c1c(N)cccc1S(=O)c1ccc([N+](=O)[O-])cc1
2-amino-N-(2-methoxyphenyl)-6-((4-nitrophen-yl)sulfinyl)benzamide
المردود 44.3%

المذيبات

ظروف التفاعل

درجة الحرارة
66°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction was quenched with MnO2 at RT
  2. 2
    ترشيحThe mixture was filtered
  3. 3
    غسيلthe residue was washed with ethyl acetate (3×5 mL)
  4. 4
    تركيزThe liquid layer was concentrated under reduced pressure
  5. 5
    أخرىthe oily residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)
  6. 6
    أخرىto provide a yellow solid

الإجراء التجريبي

Compound 25 (1.0 equiv.) was dissolved in CH3OH (30 mL) with a magnetic stirrer at RT, and 35% H2O2 (3.0 equiv.) was added slowly to this solution. This reaction mixture was heated in an oil bath at 66° C. and monitored using TLC. The reaction was quenched with MnO2 at RT. The mixture was filtered and the residue was washed with ethyl acetate (3×5 mL). The liquid layer was concentrated under reduced pressure and the oily residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a yellow solid; 44.3% yield;

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09402819B2uspto-grants-2016_08