Potassium Hydroxide → HCID 86719690, compound

HRID 922663Notes

Reaction equation

HRID 922663 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[Br:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1.Br[CH2:23][C:24]1[CH:37]=[CH:36][C:35]2[C:34](=[O:38])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](=[O:39])[C:26]=2[CH:25]=1>CN(C=O)C.C(#N)C>[Br-:10].[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH2:11][N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]([C:25]2[C:26]3[C:27](=[O:39])[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:34](=[O:38])[C:35]=3[CH:36]=[CH:37][C:24]=2[CH3:23])[CH:4]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 703202-BromomethylnaphthaleneHCID 1400184,5-DichloroimidazoleHCID 3444522-Bromomethyl-anthraquinone

Product 1

HCID 86719690HCID 86719690, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4,5-Dichloroimidazole (1.37 g, 10.0 mmol) and potassium hydroxide (0.61 g, 11.0 mmol) were placed in a round bottom flask and 10 mL acetonitrile was added. The mixture was refluxed for 30 min. The flask was removed from the head and 2-(bromomethyl)naphthalene (2.21, 10.0 mmol) was added. The mixture was returned to heat and refluxed for 2.5 h, during which time a white precipitate formed. The mixture was filtered hot, and upon cooling a precipitate formed in the filtrate. The solid, the mono-substituted imidazole, was collected by a second filtration. This solid (0.28 g, 1.0 mmol) and 2-(bromomethyl)anthraquinone (0.90 g, 3.0 mmol) will be placed in a high-pressure vessel and dissolved in the minimum volume of DMF. The solution will be heated to 100° C. for 8 h. Removal of the volatile components under reduced pressure will yield the product.

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. additionwas added
  3. temperatureto heat
  4. temperaturerefluxed for 2.5 h, during which time a white precipitate
  5. customformed
  6. filtrationThe mixture was filtered hot
  7. temperatureupon cooling a precipitate
  8. customformed in the filtrate
  9. filtrationThe solid, the mono-substituted imidazole, was collected by a second filtration
  10. customRemoval of the volatile components under reduced pressure
  11. customwill yield the product

Sources & evidence

ORD record
ord-15b35d90d2fa4585bc779f8fdcaadba5
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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