2-(Chloromethyl)anisole → N-[4-(2-methoxybenzyloxy)-phenyl]-N'-methyl-N'-methoxyurea

Participants

Reaction Steps

To an ethanolic solution of sodium ethoxide prepared from ethanol (200 ml) and sodium (2.5 g), N-(4-hydroxyphenyl)-N'-methyl-N'-methoxyurea (20 g) is added, and a solution of 2-methoxybenzyl chloride (17 g) in N,N-dimethylformamide (50 ml) is added dropwise thereto. The reaction mixture is gradually heated, kept under reflux for 3 hours and cooled to room temperature. The reaction mixture is poured onto cold water (1 liter). The precipitated crystals are collected by filtration, washed with water, dried and recrystallized from ethanol to give N-[4-(2-methoxybenzyloxy)-phenyl]-N'-methyl-N'-methoxyurea (Compound No. 23) (12 g) as white scales. M.P., 98° C.

Provenance & Evidence