Reacción #8589

Ecuación de reacción

nitric acid

aniline

cyanamide

→

N-phenylguanidinium nitrate

Rendimiento 32.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturaat reflux for 3.5 hours
3. 3
   ConcentraciónThe mixture was concentrated in vacuo
4. 4
   Otrothe residue was crystallized from methanol/ethyl acetate/dichloromethane

Procedimiento

To a room temperature solution of aniline (10.0 g, 107 mmol) in ethanol (100 mL) was added cyanamide (9.6 mL, 50 wt% in water, 123 mmol) followed by the dropwise addition of concentrated nitric acid (7.56 mL). The mixture was heated at reflux for 3.5 hours and allowed to cool to room temperature. The mixture was concentrated in vacuo and the residue was crystallized from methanol/ethyl acetate/dichloromethane to yield N-phenylguanidinium nitrate (6.7 g, 32%) as a white crystalline solid. 1H NMR (DMSO-d6): δ 9.63 (s, 1 H), 7.44 (t, 2 H), 7.37 (broad s, 3 H), 7.29 (t, 1 H), 7.23 (d, 2 H); 13C NMR (DMSO-d6): δ 156.36, 135.99, 130.40, 127.19, 125.18; MS m/z 136 (M+1 of free base).

Fuente