Ammonia → 1-[4-(2-Aminoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

HRID 723341Notes

Reaction equation

HRID 723341 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.[NH3:30].[I-].[Na+]>C(#N)C>[NH2:30][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 222Ammonia2×HCID 5238Sodium IodideHCID 120958581-[4-(2-Bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Product 1

HCID 218734911-[4-(2-Aminoethoxy)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 ammonia solution (1 ml) and sodium iodide (5 mg) and 24 hours. After repeated addition of the ammonia solution, the reaction was kept at 40° C. for 5 hours. The cooled reaction solution was filtered and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 387.44 (C24H21N3O3); MS (ESI): 388 ([M+H]+), was obtained as hydroformate in this way.

Workup

  1. customThe cooled reaction solution
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. customMS (ESI): 388 ([M+H]+), was obtained as hydroformate in this way

Sources & evidence

ORD record
ord-50bd8656bb7b435bbfc2edaa149b5d24
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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