Triethylamine → HCID 20232130, compound

Participants

Reaction Steps

To a stirred solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.28 g) in DMF (30 ml) was added dropwise a solution of mixed anhydride prepared from N-t-butoxycarbonylglycine (3.912 g), triethylamine (2.371 g) and ethyl chloroformate (2.425 g) in methylene chloride (15 ml) with stirring under ice-cooling. The stirring was continued for 1 hour at the same temperature. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed successively with water, an aqueous solution of sodium bicarbonate and water, dried and evaporated in vacuo. The residue was dissolved in methanol (12 ml) and conc. ammonia (1.5 ml) was added thereto. After stirring for 2 hours at room temperature, the resulting precipitates were collected by filtration, washed with methanol, and dried to give 6-[4-[N-(t-butoxycarbonyl)glycylamino]phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.74 g).

Provenance & Evidence