Water → 1-(3-Iodophenyl)-1,3-dihydro-2h-imidazol-2-one

HRID 857124Notes

Reaction equation

CO[CH:3](OC)[CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[CH:10]=1)=[O:7].O>C(O)(=O)C>[I:15][C:11]1[CH:10]=[C:9]([N:8]2[CH:3]=[CH:4][NH:5][C:6]2=[O:7])[CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N(2,2-Dimethoxyethyl)-N′-(3-iodophenyl)urea (618 mg) was dissolved in acetic acid (10 ml) and water (1 ml) and the mixture was stirred at 20° C. for 17 h and then heated to 100° C. for 0.5 h. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. The solution was washed with NaHCO3 solution, dried and purified by chromatography on 10 g silica Bond Elut cartridge eluting with EtOAc-petroleum ether (1:7 to 1:1) to give the title compound (130 mg) LCMS RT=2.66 min.

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate
washThe solution was washed with NaHCO3 solution
customdried
custompurified by chromatography on 10 g silica Bond Elut cartridge
washeluting with EtOAc-petroleum ether (1:7 to 1:1)

Sources & evidence

ORD record: ord-3c02eb8592054997a1ceaf4816352414
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144908B2

Reaction notes

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