Реакция #8591

Уравнение реакции

nitric acid

3,4,5-trimethoxyaniline

cyanamide

→

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

Выход 46.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураat reflux for 13 hours
3. 3
   КонцентрированиеThe mixture was concentrated in vacuo to approximately 70% of its original volume and ether
4. 4
   workup.ADDITIONwas added
5. 5
   ДругоеThe resulting precipitate was isolated on
6. 6
   Фильтрацияa filter

Методика

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).

Источник