Reaction #8591

Reaction equation

nitric acid

3,4,5-trimethoxyaniline

cyanamide

→

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

Yield 46.0%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureat reflux for 13 hours
3. 3
   ConcentrationThe mixture was concentrated in vacuo to approximately 70% of its original volume and ether
4. 4
   workup.ADDITIONwas added
5. 5
   OtherThe resulting precipitate was isolated on
6. 6
   Filtrationa filter

Procedure

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).

Source