تفاعل #816384

ord-22c82afce8d54930a866fb61ee4a8c3d

معادلة التفاعل

O=[N+]([O-])c1ncc[nH]1
2-nitroimidazole
Cc1ccc(S(=O)(=O)CCCS(=O)(=O)c2ccc(C)cc2)cc1
1,3-ditosylpropane
Cc1ccc(S(=O)(=O)CCCc2c[nH]c([N+](=O)[O-])n2)cc1
3-tosylpropyl-(2-nitroimidazole)

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
80°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONwas added
  2. 2
    أخرىThe solvent was evaporated under vacuum
  3. 3
    ترشيحThe solid was filtered
  4. 4
    تركيزthe solvent was concentrated
  5. 5
    غسيلeluted with hexane:ethylacetate (1:1)

الإجراء التجريبي

To a stirred mixture containing 2-nitroimidazole (1 g, 8.34 mmol) and Cs2,CO3 (2.9 g, 8.90 mmol) in dimethylformaide (DMF, 50 ml), 1,3-ditosylpropane (3.84 g, 9.99 mmol) was added. The reaction was heated at 80° C. for 3 hours. The solvent was evaporated under vacuum and the residue was suspended in ethylacetate. The solid was filtered, the solvent was concentrated, loaded on a silica gel-packed column and eluted with hexane:ethylacetate (1:1). The product, 3-tosylpropyl-(2-nitroimidazole), was isolated (1.67 g, 57.5%) with m.p. 108-111° C. 1H-NMR (CDCl3) δ 2.23 (m, 2H), 2.48 (S, 3H), 4.06 (t, 2H, J=5.7 Hz), 4.52 (t, 2H, J=6.8 Hz), 7.09 (S, 1H), 7.24 (S, 1H), 7.40 (d, 2H, J=8.2 Hz), 7.77 (d, 2H, J=8.2 Hz).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07582281B2uspto-grants-2009_09