Реакция #8589

Уравнение реакции

nitric acid

aniline

cyanamide

→

N-phenylguanidinium nitrate

Выход 32.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураat reflux for 3.5 hours
3. 3
   КонцентрированиеThe mixture was concentrated in vacuo
4. 4
   Другоеthe residue was crystallized from methanol/ethyl acetate/dichloromethane

Методика

To a room temperature solution of aniline (10.0 g, 107 mmol) in ethanol (100 mL) was added cyanamide (9.6 mL, 50 wt% in water, 123 mmol) followed by the dropwise addition of concentrated nitric acid (7.56 mL). The mixture was heated at reflux for 3.5 hours and allowed to cool to room temperature. The mixture was concentrated in vacuo and the residue was crystallized from methanol/ethyl acetate/dichloromethane to yield N-phenylguanidinium nitrate (6.7 g, 32%) as a white crystalline solid. 1H NMR (DMSO-d6): δ 9.63 (s, 1 H), 7.44 (t, 2 H), 7.37 (broad s, 3 H), 7.29 (t, 1 H), 7.23 (d, 2 H); 13C NMR (DMSO-d6): δ 156.36, 135.99, 130.40, 127.19, 125.18; MS m/z 136 (M+1 of free base).

Источник