Trimethylamine → HCID 20510897, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 10.4 g of crude ethyl 5-(bromomethyl)-1,3-diacetyl-2,3-dihydro-2-oxo-1H-imidazole-4-carboxylate in 100 ml of dry tetrahydrofuran, cooled in an ice bath under argon, there is added gaseous trimethylamine for 7 minutes. The mixture is stirred at 0° C. for 15 minutes and then evaporated to dryness. To the residue is added 50 ml of 31% hydrogen bromide in acetic acid and the mixture is warmed briefly on a steam bath to about 50° C. to bring about dissolution. It is then allowed to stand at room temperature for 1 hour before it is evaporated to dryness. Water (50 ml) is added to the residue and the resultant aqueous mixture is washed with methylene chloride, treated with charcoal, filtered through diatomaceous earth, and evaporated to dryness. The resultant residue is crystallized from a mixture of ethanol and ethyl acetate (1:3) and then recrystallized from ethanol to give 5-(ethoxycarbonyl)-2,3-dihydro-N,N,N-trimethyl-2-oxo-1H-imidazole-4-methanaminium bromide monohydrate melting at about 199°-200° C. (dec.). This compound has the following structural formula: ##STR7##

Provenance & Evidence