تفاعل #91503

معادلة التفاعل

NaOH

N-(2,2-diethoxyethyl)carbodiimide

Aniline

methanesulfonic acid

→

guanidine

المردود 73.8%

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

المردود 73.8%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was warmed
2. 2
   درجة الحرارةat reflux for 24 h
3. 3
   استخلاصextracted with CH2Cl2
4. 4
   أخرىDrying
5. 5
   تركيزconcentration
6. 6
   أخرىafforded a product that

الإجراء التجريبي

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)+.

المصدر