Methyl iodide → HCID 178489507, compound

Participants

Reaction Conditions

Reaction Steps

0.970 g (3.475 mmol) N-(5-iodopyridin-2-yl)thiourea was dissolved in 30 mL methanol, 0.30 mL (4.777 mmol) methyl iodide in 2 mL methanol was added dropwise, and the mixture was heated at 60° C. (oil bath temperature) for 20 min and subsequently stirred at room temperature for 18 hr. The solvent was removed under vacuum, and the intermediate product was redissolved in 30 mL ethanol. 1.50 mL (11.262 mmol) 2-methoxybenzylamine was added dropwise and heated for 1.5 hr at 85° C. (oil bath temperature). The solvent was then evaporated under vacuum. The crude product was redissolved in dichloromethane and extracted with water (2×50 mL). The organic phase was then extracted again with 2 N sodium hydroxide solution (1×50 mL) and washed with water (1×50 mL) to remove iodide salt from the product. After drying over magnesium sulfate and overlayering with pentane the product was crystallized. 1.252 g (3.080 mmol, 89%) N-(5-iodopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine was obtained. For additional purification, a portion of the first crystallizate was again recrystallized from dichloromethane/water.

Provenance & Evidence