2,4-Dichlorobenzylamine → N-[(2,4-dichlorophenyl)methyl]-3-ethyl-1-methyl-2-oxo-4-imidazolidinecarboxamide

A mixture of 3-ethyl-1-methyl-2-oxo-4-imidazolidinecarboxylic acid (138 mg, 0.800 mmol), 1-hydroxybenzotriazole hydrate (147 mg, 0.960 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (184 mg, 0.960 mmol) and N-ethyl morpholine (0.409 ml, 3.20 mmol) in dichloromethane (9 ml) was stirred at room temperature for 10 minutes. A solution of [1-(2,4-dichlorophenyl)methyl]amine (141 mg, 0.8 mmol) in dichloromethane (1 ml) was added and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (10 ml) and the solution was washed with saturated sodium hydrogen carbonate solution (10 ml), water (10 ml), citric acid solution (10 ml) and brine (10 ml), dried and evaporated. The residue was purified by mass-directed automated HPLC. The residue was triturated with ether and the resulting solid was collected and dried to give N-[(2,4-dichlorophenyl)methyl]-3-ethyl-1-methyl-2-oxo-4-imidazolidinecarboxamide (141 mg, 53%). LC/MS [M+H]+=330, retention time=2.36 minutes.

1. stirringthe reaction mixture was stirred at room temperature for 18 hours
2. washthe solution was washed with saturated sodium hydrogen carbonate solution (10 ml), water (10 ml), citric acid solution (10 ml) and brine (10 ml)
3. customdried
4. customevaporated
5. customThe residue was purified
6. customThe residue was triturated with ether
7. customthe resulting solid was collected
8. customdried

ORD record

ord-d6bb53d20af344028ecb74b6934ff447

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932282B2