Maleic Acid → 4-[5-(2-methoxyphenoxy)pentoxy]benzenecarboximidamide (Z)-2-butenedioate

Participants

Reaction Conditions

Reaction Steps

4-[5-(2-Methoxyphenoxy)pentoxy]benzenecarboximidamide is dissolved in ethanol (2 B anhydrous, 9.6 L) with warming to 55° C. and this solution is filtered into a 10 gallon resin flask. The filtrate whose temperature is now 50° C. is admixed with a warm (~45° C.), filtered solution of maleic acid (0.488 kg, 4.20 mol) in 2 B anhydrous ethanol (4.15 L) rapidly. The product precipitates almost immediately and temperature rises to approximately 60°-65° C. The mixture is cooled to 5° C. with an ice bath for 2 hours and then filtered. The filter cake is washed with 2 B anhydrous ethanol (2×1 L) and then dried in vacuo (71° C., 3 mm Hg) for 16 hours to yield 4-[5-(2-methoxyphenoxy)pentoxy]benzenecarboximidamide (Z)-2-butenedioate, m.p. 163°-165° C.

Provenance & Evidence