Hydrogen Bromide → 1,3-dihydro-4-(4-methoxybenzoyl)-5-(methoxymethyl)-2H-imidazol-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4.0 g of 5-(bromomethyl)-1,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one in 50 ml of dry tetrahydrofuran is cooled to -78° C. under argon, 1.0 ml of dry methanol is added by syringe, and the solution is allowed to warm to 25° C. over 1.5 hours. Concentrated hydrobromic acid (1 ml) is then added and the mixture is stirred at 25° C. overnight. The solvent is then evaporated and the residual solid is recrystallized twice from a mixture of methanol and water to give 1,3-dihydro-4-(4-methoxybenzoyl)-5-(methoxymethyl)-2H-imidazol-2-one melting at about 211°-212° C. with decomposition. This compound has the following structural formula: ##STR6##

Provenance & Evidence