Sodium Hydroxide → HCID 13458487, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 31.95 g (0.15 mole) of 2-iminoimidazolidine monohydroiodide in 400 ml THF was treated with 11.99 g (0.15 mole) 50% NaOH solution and stirred for 0.5 hour. Twenty grams of anhydrous Na2SO4 were added and the mixture stirred an additional 0.5 hour. After cooling to -20° C. (it was necessary to maintain a temperature of -20° C. at all times when in the free base form) under N2, a solution of 9.99 g (0.075 mole) of 3-methylphenyl isocyanate in 125 ml THF was added dropwise over a 3-hour period, maintaining a temperature of -20° C. The mixture was stirred an additional hour, then the inorganics were filtered off and the solvent was removed in vacuo, cold, to yield a yellow oil, which was stirred in cold brine and extracted with 3×150 ml portions of cold CH2Cl2. The combined CH2Cl2 extracts were dried over anhydrous K2CO3 and filtered. The filtrate was acidified to pH<3 with excess ethereal HCl, adding MeOH to dissolve solids which formed upon acidification. The solution was stored in a freezer overnight. The solvent and excess HCl were removed in vacuo to leave a yellow-orange oil, which solidified when washed with Et2O. The solid was recrystallized from MeOH/Et2O to yield 11.11 g of impure product which was converted to the free base and then back to the HCl salt, and recrystallized from MeOH/Et2O to yield 7.99 g (41.8%) of pure hydrochloride salt, a white solid, m.p. 195°-196.5° C. (dec.).

Provenance & Evidence