反応 #91503

反応方程式

NaOH

N-(2,2-diethoxyethyl)carbodiimide

Aniline

methanesulfonic acid

→

guanidine

収率 73.8%

1-(2,2-Diethoxyethyl)-3-phenylguanidine

収率 73.8%

溶媒

ethanol

反応条件

後処理

1. 1
   温度the mixture was warmed
2. 2
   温度at reflux for 24 h
3. 3
   抽出extracted with CH2Cl2
4. 4
   その他Drying
5. 5
   濃縮concentration
6. 6
   その他afforded a product that

実験手順

Aniline (1.66 g, 17.8 mmol) was dissolved in ethanol (25 mL), and N-(2,2-diethoxyethyl)carbodiimide (a), (2.82 g, 17.8 mmol), was added dropwise. Then methanesulfonic acid (1.71 g, 17.8 mmol) was added, and the mixture was warmed at reflux for 24 h. The reaction mixture was poured into NaOH (0.5 M) and extracted with CH2Cl2. Drying and concentration afforded a product that was subjected to flash chromatography to give the intermediate guanidine (b) (3.3 g, 73.8%). 1H NMR (500 MHz, DMSO-d6) δ 7.27-6.90 (m, 5H), 4.55 (t, 1H), 3.76-3.70 (m, 2H), 3.60-3.54 (m, 2H), 3.35-3.34 (d, 2H), 1.22 (pent, 6H). MS: 249.8 (M−H)−; 252.1 (M+H)+.

出典