Sodium Iodide → 1-[4-(2-Methylaminoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

HRID 723340Notes

Reaction equation

HRID 723340 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[C:12]2=[O:29])=[CH:7][CH:6]=1.[CH3:30][NH2:31].[I-].[Na+]>C(#N)C>[CH3:30][NH:31][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[C:12]2=[O:29])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6329MethylamineHCID 120958581-[4-(2-Bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Product 1

HCID 218733931-[4-(2-Methylaminoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[4-(2-bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (50 mg) in acetonitrile (1 ml) was left to stand with methylamine (1M in THF, 1 ml) and sodium iodide (5 mg) and 24 hours. The reaction solution was filtered and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 401.47 (C24H23N3O3); MS (ESI): 402 ([M+H]+), was obtained as hydroformate in this way.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by preparative HPLC
  4. customMS (ESI): 402 ([M+H]+), was obtained as hydroformate in this way

Sources & evidence

ORD record
ord-dd2803893ae4422e8ae8e7fcda91c4ca
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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