Reacción #8592

Ecuación de reacción

nitric acid

4-methoxyaniline

cyanamide

→

N-(4Methoxyphenyl)guanidinium nitrate

Rendimiento 38.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturaat reflux for 3 hours
3. 3
   OtroThe resulting crystals were isolated on
4. 4
   Filtracióna filter

Procedimiento

To a room temperature solution of 4-methoxyaniline (10.0 g, 81.19 mmol) in ethanol (100 mL) was added cyanamide (7.24 mL, 50 wt % in water, 93.37 mmol) followed by the dropwise addition of concentrated nitric acid (5.71 mL). The mixture was heated at reflux for 3 hours and allowed to cool to room temperature. The resulting crystals were isolated on a filter to yield N-(4Methoxyphenyl)guanidinium nitrate (7.1 g, 38%) as a violet crystals. 1H NMR (DMSO-d6): δ 9.39 (s, 1 H), 7.22 (s, 3 H), 7.17 (d, 2 H), 6.99 (d, 2 H)<3.76 (s, 3 H); 13C NMR (DMSO-d6) δ 158.17, 156.26, 127.48, 127.27, 114.90, 55.40; MS m/z 166 (M+1 of free base).

Fuente