تفاعل #595403

ord-15b1b61ada9045ca87e52e6382d6f1e9

معادلة التفاعل

[K+].[OH-]
KOH
C=CCCBr
4-Bromo-1-butene
O=[N+]([O-])c1ccccc1S(=O)(=O)Nc1ccccc1
2-nitro-N-phenylbenzenesulfonamide
C=CCCN(c1ccccc1)S(=O)(=O)c1ccccc1[N+](=O)[O-]
white solid
المردود 64.7%
C=CCCN(c1ccccc1)S(=O)(=O)c1ccccc1[N+](=O)[O-]
N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide
المردود 64.7%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGwas stirred at room temperature overnight
  2. 2
    غسيلwashed with 1M HCl 2×10 mL and water 3×10 mL
  3. 3
    تجفيفThe organic layer was dried over anhydrous Na2SO4
  4. 4
    أخرىevaporated
  5. 5
    أخرىto afford the crude product, which

الإجراء التجريبي

Crushed KOH (0.0484 g, 0.862 mmol, 1.2 equiv) was added to 2-nitro-N-phenylbenzenesulfonamide (0.200 g, 0.719 mmol) in 1 mL DMF, and the mixture was stirred for 30 min. 4-Bromo-1-butene (0.2426 g, 1.80 mmol) in 2 mL DMF solution was added dropwise into the mixture and it was stirred at room temperature overnight. The reaction mixture was diluted with 30 mL EtOAc and washed with 1M HCl 2×10 mL and water 3×10 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 0.1546 g white solid, yield 63.5%.

المصدر

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