Reacción #8591

Ecuación de reacción

nitric acid

3,4,5-trimethoxyaniline

cyanamide

→

N-(3,4,5-trimethoxyphenyl)guanidinium nitrate

Rendimiento 46.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturaat reflux for 13 hours
3. 3
   ConcentraciónThe mixture was concentrated in vacuo to approximately 70% of its original volume and ether
4. 4
   workup.ADDITIONwas added
5. 5
   OtroThe resulting precipitate was isolated on
6. 6
   Filtracióna filter

Procedimiento

To a room temperature solution of 3,4,5-trimethoxyaniline (3.46 g,18.9 mmol) in ethanol (20 mL) was added cyanamide (1.68 mL, 50 wt % in water, 21.7 mmol) followed by the dropwise addition of concentrated nitric acid (1.33 mL). The mixture was heated at reflux for 13 hours and allowed to cool to room temperature. The mixture was concentrated in vacuo to approximately 70% of its original volume and ether was added. The resulting precipitate was isolated on a filter to yield N-(3,4,5-trimethoxyphenyl)guanidinium nitrate (2.5 g, 46%) as a grey powder. 1H NMR (DMSO-d6): δ 9.47 (s, 1 H), 7.29 (s, 3 H), 6.57 (s, 2 H), 3.80 (s, 6 H), 3.68 (s, 3 H); C NMR (DMSO-d6): δ 155.78, 153.33, 136.07, 130.58, 102.90, 59.99, 55.96; MS m/z226 (M+1 of free base).

Fuente