Ammonia → 3-Methoxy-4-(4-phthalimidomethylbenzyloxy)benzamidine

Participants

Reaction Steps

To a mixture of 100 ml of chloroform and 100 ml of anhydrous methanol, was added 3.0 g of methyl 3-methoxy-4-(4-phthalimidomethylbenzyloxy)benzimidate hydrochloride followed by 16 ml of a methanol solution of anhydrous ammonia (22 mg/ml). The mixture was stirred for 24 hours and then evaporated to dryness. The residue was dissolved in methanol, then poured into a large volume of chloroform, and filtered from precipitated colorless solids. The filtrate was evaporated to dryness and the residue was recrystallized from methanol to yield 1.4 g of 3-methoxy-4-(4-phthalimidomethylbenzyloxy)benzamidine; m.p. 228°-230° C. To obtain a methanesulfonate, the above benzamidine compound was suspended in methanol and admixed with an excess of methanesulfonic acid. Upon addition of ether to the resulting solution, there was obtained a colorless solid which was recrystallized from methanol to yield colorless needle crystals of 3-methoxy-4-(4-phthalimidomethylbenzyloxy)benzamidine methanesulfonate; m.p. 174°-176° C.

Provenance & Evidence