2-Imidazolidinone → HCID 20669979, compound

Temperature

45 °C

A solution of imidazolidin-2-one (0.75 g, 8.71 mmol) in DMF (17 mL) was treated drop-wise with LiHMDS (1M THF, 10.45 mL, 10.45 mmol), stirred for 2 h, treated with bromoacetonitrile (0.607 mL, 8.71 mmol) and heated at 45° C. overnight. The mixture was cooled to RT, treated with satd. NH4Cl, extracted with EtOAc (4×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 2-(2-oxoimidazolidin-1-yl)acetonitrile (65 mg, 6%). 1H NMR (400 MHz, DMSO-d6): δ 6.38 (s, 1 H), 4.66 (s, 2 H), 3.98-3.93 (m, 2H), 3.91-3.86 (m, 2H); MS (ESI) m/z: 126.1 (M+H+).

1. temperatureThe mixture was cooled to RT
2. additiontreated with satd
3. extractionNH4Cl, extracted with EtOAc (4×)
4. washthe combined organics were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated to dryness
7. custompurified via silica gel chromatography (MeOH/DCM)

ORD record

ord-484303ba076f4eb79ded8c3e8990de87

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133183B2