Reacción #816384

Ecuación de reacción

2-nitroimidazole

1,3-ditosylpropane

→

3-tosylpropyl-(2-nitroimidazole)

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe solvent was evaporated under vacuum
3. 3
   FiltraciónThe solid was filtered
4. 4
   Concentraciónthe solvent was concentrated
5. 5
   Lavadoeluted with hexane:ethylacetate (1:1)

Procedimiento

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).

Fuente