Sodium Iodide → HCID 12095856, compound

HRID 723331Notes

Reaction equation

HRID 723331 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([N:18]2[CH:22]=[CH:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)[C:19]2=[O:36])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.[I-].[Na+]>C(#N)C>[CH2:1]([C:8]1[CH:9]=[C:10]([N:18]2[CH:22]=[CH:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)[C:19]2=[O:36])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 31268PyrrolidineHCID 12095857HCID 12095857, compound

Product 1

HCID 12095856HCID 12095856, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[3-benzyl-4-(2-bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (60 mg) in acetonitrile (1 ml) was mixed with pyrrolidine (0.2 ml) and sodium iodide (5 mg) and boiled under reflux for 2 hours. The cooled solution was filtered and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 531.66 (C34H33N3O3); MS (ESI): 532 ([M+H]+), was obtained as hydroformate in this way.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe cooled solution was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. customMS (ESI): 532 ([M+H]+), was obtained as hydroformate in this way

Sources & evidence

ORD record
ord-17598ad5656a47d3ab06844c2a1b4a70
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

Loading…