Reacción #8805

Ecuación de reacción

nitrile

3-(1,3-dioxolan-2-yl)thiophene-2-carbonitrile

hydroxylamine hydrochloride

sodium carbonate

→

3-(1,3-dioxolan-2-yl)thiophene-2-amidoxime

Disolventes

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   OtroThe colourless precipitate was isolated by filtration
3. 3
   Otrodried under a stream of air
4. 4
   Otroazeotroped with toluene (2×)

Procedimiento

To a solution of the foregoing nitrile (5.0 g, 27.59 mmol) in ethanol (20 ml) was added a solution of hydroxylamine hydrochloride (3.7 equivalents) and sodium carbonate (1.7 equivalents) in water (50 ml). The resulting mixture was heated to 40° C. for 5 h, then cooled to room temperature. The colourless precipitate was isolated by filtration, dried under a stream of air and azeotroped with toluene (2×) to give 3-(1,3-dioxolan-2-yl)thiophene-2-amidoxime as an off-white solid (4.36 g). 1H NMR (DMSO-d6): δ 9.83 (1H, s), 7.48 (1H, d, J 5.18), 7.15 (1H, d, J 5.18), 6.05 (1H, s), 5.77 (2H, bs), 4.05 (2H, m), 3.91 (2H, m).

Fuente