تفاعل #595404

ord-14062753e3f8462db3c4fd2416e1f840

معادلة التفاعل

O=C(OO)c1cccc(Cl)c1
mCPBA
C=CCCN(c1ccccc1)S(=O)(=O)c1ccccc1[N+](=O)[O-]
N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide
O=[N+]([O-])c1ccccc1S(=O)(=O)N(CCC1CO1)c1ccccc1
colorless oil
المردود 97.0%
O=[N+]([O-])c1ccccc1S(=O)(=O)N(CCC1CO1)c1ccccc1
2-nitro-N-(2-(oxiran-2-yl)ethyl)-N-phenylbenzenesulfonamide
المردود 97.0%

المذيبات

ظروف التفاعل

درجة الحرارة
0°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةgradually warmed up to room temperature
  2. 2
    workup.STIRRINGto stir for 18 hr
  3. 3
    تجفيفThe organic layer was dried over anhydrous Na2SO4
  4. 4
    أخرىevaporated
  5. 5
    أخرىto afford the crude product, which

الإجراء التجريبي

mCPBA (77%, 0.0550 g, 0.246 mmol) was added to N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide (0.0653 g, 0.196 mmol) in 1 mL CHCl3 at 0° C. The mixture was stirred at 0° C. for 30 min, then gradually warmed up to room temperature and continued to stir for 18 hr. After TLC showed the disappearance of starting material, the reaction mixture was diluted with a 1:1 mixture of water and saturated NaHCO3 (2×10 mL) and water (10 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.0662 g colorless oil as product, yield 96.9%.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09095572B2uspto-grants-2015_08