Bromine → HCID 178518095, compound

HRID 1987959Notes

Reaction equation

HRID 1987959 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][NH:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8].BrBr.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12]([NH:29][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=3)=[N:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 24408BromineHCID 673264-FluorobenzylamineHCID 13665722HCID 13665722, compound

Product 1

HCID 178518095HCID 178518095, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 1-(3,4-dichloro-phenyl)-5-phenyl-1,3-dihydro-imidazol-2-one (1 equiv., 0.33 mmol, 100 mg) in chloroform (5 mL) was added dropwise Br2 (1.1 equiv., 0.36 mmol, 19 μL) in chloroform (2 mL) at 0° C. under nitrogen. After 10 min, 4-fluorobenzylamine (10 equiv., 3.28 mmol, 372 μL) was added in situ at 0° C. The reaction mixture was allowed to warm up to room temperature and heated at reflux overnight. After evaporation of solvent, the residue was purified by column chromatography (SiO2, n-heptane/ethyl acetate: 0-100%) affording the title compound as a white solid (32 mg, 23%). δH NMR (DMSO, 300 MHz) 8.83 (1H, br, s, NH), 7.91 (1H, d, J=2.4 Hz, H arom), 7.46-7.08 (11H, m, H arom), 6.16 (1H, s, C5H), 4.44 (2H, s, CH2Ph); m/z (EI) 431.0 (12%), 430.0 (74), 429.1 (26), 428.0 (100, M+H+).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customAfter evaporation of solvent
  4. customthe residue was purified by column chromatography (SiO2, n-heptane/ethyl acetate: 0-100%)

Sources & evidence

ORD record
ord-c99b6be3a52b46c79b335b9fb304bc96
Source dataset
uspto-grants-2009_06
Patent number
US07553862B2

Reaction notes

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