反应详情

温度

70 °C

0.800 g (5.117 mmol) N-pyridin-2-yl-thiourea was dissolved in 10 mL methanol, 0.45 mL (7.164 mmol) methyl iodide in 5 mL methanol was added dropwise, and the mixture was heated for 1 hr at 70° C. (oil bath temperature) and subsequently stirred at room temperature. The solvent was removed under vacuum and the intermediate product, methyl N-(pyridin-2-yl)imidothiocarbamate hydroiodide, was redissolved in 15 mL ethanol. 1.36 mL (10.235 mmol) 2-methoxybenzylamine was added dropwise, and the mixture was heated for 2.75 hr at 85° C. (oil bath temperature) and subsequently stirred at room temperature. The solvent was then evaporated under vacuum. The crude product was redissolved with dichloromethane and extracted with water (2×30 mL). After drying over magnesium sulfate and removal of the solvent, purification was carried out via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid). For complete ion exchange with the ion exchanger (Fluka, acetate on 1.5 mmol CH3COO/g/resign polymer substrate), the purified N-(2-methoxybenzyl)-N′-pyridin-2-yl-guanidine was converted to the acetate salt in a yield of 0.357 g (1.128 mmol).

1. customThe solvent was removed under vacuum
2. dissolutionthe intermediate product, methyl N-(pyridin-2-yl)imidothiocarbamate hydroiodide, was redissolved in 15 mL ethanol
3. temperaturethe mixture was heated for 2.75 hr at 85° C. (oil bath temperature)
4. stirringsubsequently stirred at room temperature
5. customThe solvent was then evaporated under vacuum
6. dissolutionThe crude product was redissolved with dichloromethane
7. extractionextracted with water (2×30 mL)
8. dry with materialAfter drying over magnesium sulfate and removal of the solvent, purification