Reaktion #8591

Reaktionsgleichung

nitric acid

3,4,5-trimethoxyaniline

cyanamide

→

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

Ausbeute 46.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle