1-(4-AMINOPHENYL)-3-METHYLIMIDAZOLIDIN-2-ONE synthesis

Yield:95182-37-9 53%

Reaction Conditions:

with copper(l) iodide;potassium carbonate;N,N`-dimethylethylenediamine in toluene at 140; for 2 h;Microwave irradiation;

Steps:

C-3

C-3) 1 -(4- Aminophenyl)-3 -methyl- imidazo lidin-2-one200 mg (1.16 mmol, 1 eq) 4-bromoaniline, 122 mg (1.22 mmol, 1.05 eq) l-methyl-2- imidazolidinone as well as 22 mg copper(I)-iodide (0.12 mmol, 0.1 eq) are suspended in 2 mL toluene. After the addition of 24.7 μL (0.23 mmol, 0.2 eq) λ^λT-dimethyl- ethylenediamine and 321 mg (2.33 mmol, 2 eq) potassium carbonate the reaction mixture is heated in the microwave for 2 h at 140⁰C with stirring. After cooling, 2 mL MeOH are added, the homogeneous mixture is mixed with water and extracted 5 times with 30 mL EE. The combined organic phases are dried and all the volatile constituents are eliminated in vacuo. Purification by column chromatography (normal phase, silica gel, DCM/MeOH/NH₃ 100/0/ auf 80/20/2) yields 118 mg (0.62 mmol, 53 %) C-3. Rf = 0.20 (silica gel, DCM/MeOH/NH₃ 95/5/0.5) MS-ESI⁺: 192 (M+H)⁺

References:

WO2008/77885,2008,A2 Location in patent:Page/Page column 21