Potassium Hydroxide → HCID 21873464, compound

HRID 723353Notes

Reaction equation

HRID 723353 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[CH3:11][N:12]([CH3:35])[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:26]=[CH:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[C:23]2=[O:34])=[CH:18][CH:17]=1.[OH-].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH3:11][N:12]([CH3:35])[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH:26]=[CH:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]([O:33][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N+:1]([O-:3])=[O:2])=[CH:31][CH:32]=3)[C:23]2=[O:34])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 738951-Fluoro-2-nitrobenzeneHCID 21873309HCID 21873309, compound

Product 1

HCID 21873464HCID 21873464, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

2-Nitrofluorobenzene (0.14 g) was added to a mixture of 1-[4-(2-dimethylaminoethoxy)phenyl]-3-(4-hydroxyphenyl)-1,3-dihydroimidazol-2-one (0.34 g), Aliquat® 336 (0.04 g, tricaprylylmethylammonium chloride), potassium hydroxide (0.077 g) and toluene (10 mL). The mixture was heated under reflux for 3 hours. After cooling, the reaction solution was washed with water, dried and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 460.49 (C25H24N4O5); MS (ESI): 461 ([M+H]+), was obtained as hydrotrifluoroacetate in this way.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. washthe reaction solution was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC
  8. customMS (ESI): 461 ([M+H]+), was obtained as hydrotrifluoroacetate in this way

Sources & evidence

ORD record
ord-1fd1d3dfba3943b8a732453c75c32217
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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