1,3-Dihydro-2H-imidazol-2-one

light pink liquid

1,3-dihydro-2H-imidazol-2-one is an imidazolinone.

To a solution of 2-bromo-6-(4-isopropyl-4i/-l, 2, 4-triazol-3-yl)pyridine (200 mg, 0.75 mmol) in DMF (5 mL) was added 2, 3-dihydro- li/-imidazol-2-one (94.4 mg, 1.12 mmol), Pd2(dba)3.CHCb (77.5 mg, 0.08 mmol), Xantphos (86.6 mg, 0.15 mmol) and CS2CO3 (731.8 mg, 2.25 mmol). The resulting mixture was stirred at 60°C for 5 h under N2 atmosphere. The resulting mixture was diluted with H2O and extracted with ethyl acetate. (0291) The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by flash column chromatography with dichloromethane/methanol (10/1, v/v) to afford the title compound (100 mg, 49percent) as a yellow solid. LCMS (ESI, m/z): [M+H]+ = 271.2To a solution of lH-imidazol-2(3H)-one (56mg, 0.67mmol) in nitrobenzene (0.5ml) was added A1C13 (178mg, 1.34mmol) and 2, 4-dichlorobenzoyl chloride (140.4mg, 0.67mmol). The mixture was heated to dissolve A1C13. The mixture was microwave irradiated at 80 °C for 40 min. To the mixture was added 50ml of ether and 60ml of 0.2 N NaOH. The aqueous layer was collected and neutralized with HCl. The cloudy solution was extracted with 50 ml of EtOAc. The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexane) to give 62 mg (40percent yield) of A. Compound A (62 mg, 0.24 mmol) was dissolved in 10 ml anhydrous DMF and treated with 28mu1 (0.192 mmol) of t-butyl bromoacetate and 180 mg of K2C03 (0.36 mmol). The mixture was stirred at 50 °C overnight. After the reaction solvent was evaporated, the residues was dissolved with EtOAc and washed successively with water and brine. The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexane) to obtain B in 60percent yield (53 mg, 0.144 mmol).

Molecular Weight:84.08
XLogP3:-0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Exact Mass:84.032362755
Monoisotopic Mass:84.032362755
Topological Polar Surface Area:41.1
Heavy Atom Count:6
Complexity:87
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes