Aminoacetaldehyde dimethyl acetal → 1-(3-bromophenyl)-1,3-dihydro-2H-imidazol-2-one

A solution of 1-bromo-3-isocyanatobenzene (1.0 mL, 8.01 mmol) and [2,2-bis(methyloxy)ethyl]amine (0.86 mL, 8.01 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 16 hr. The solution was concentrated in vacuo and the residue taken up in a mixture of CH3CN (10 mL) and H2O (3 mL). TFA (3 mL) was added and the solution stirred at room temperature for 4 hr. The solution was concentrated in vacuo, the residue taken up in EtOAc then washed with satd NaHCO3, H2O, and brine. The organics were then dried over Na2SO4, concentrated in vacuo and the residue recrystallized from EtOAc to give 1-(3-bromophenyl)-1,3-dihydro-2H-imidazol-2-one as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.60 (d, J=3.0 Hz, 1H), 7.03 (d, J=3.0 Hz, 1H), 7.34-7.36 (m, 2H); 7.70-7.72 (m, 1H), 8.06 (s, 1H), 10.39 (br s, 1H).

1. concentrationThe solution was concentrated in vacuo
2. additionthe residue taken up in a mixture of CH3CN (10 mL) and H2O (3 mL)
3. additionTFA (3 mL) was added
4. concentrationThe solution was concentrated in vacuo
5. washthen washed with satd NaHCO3, H2O, and brine
6. dry with materialThe organics were then dried over Na2SO4
7. concentrationconcentrated in vacuo
8. customthe residue recrystallized from EtOAc

ORD record

ord-49cfa41c1b5744d8b42a6de6d0d382f0

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822518B2