반응 #8591

반응 방정식

nitric acid

3,4,5-trimethoxyaniline

cyanamide

→

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

수율 46.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 13 hours
3. 3
   농축The mixture was concentrated in vacuo to approximately 70% of its original volume and ether
4. 4
   workup.ADDITIONwas added
5. 5
   기타The resulting precipitate was isolated on
6. 6
   여과a filter

실험 절차

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).

출처