Methyl iodide → HCID 178422547, compound

HRID 922662Notes

Reaction equation

HRID 922662 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].Br[CH2:11][C:12]1[CH:25]=[CH:24][C:23]2[C:22](=[O:26])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:27])[C:14]=2[CH:13]=1.[I:28][CH3:29]>CN(C=O)C.C(#N)C>[I-:28].[CH3:29][N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N+:5]([C:13]2[C:14]3[C:15](=[O:27])[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:22](=[O:26])[C:23]=3[CH:24]=[CH:25][C:12]=2[CH3:11])=[CH:4]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 1400184,5-DichloroimidazoleHCID 3444522-Bromomethyl-anthraquinone2×

Product 1

HCID 178422547HCID 178422547, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

4,5-Dichloroimidazole (0.18 g, 1.33 mmol) and potassium hydroxide (0.08 g, 1.46 mmol) were combined in a round bottom flask. Acetonitrile (2 mL) was added and the mixture was stirred at reflux for 30 min, dissolving the remaining solid. Concurrently, 2-(Bromomethyl)anthraquinone (0.40 g, 1.33 mmol) was added to 30 mL acetonitrile and stirred at reflux for 30 min, partially dissolving the solid. The solution in the initial flask was added to the 2-(bromomethyl)anthraquinone mixture, and the solution was returned to reflux for 3 h. The mixture was filtered hot, and a precipitate quickly formed in the tan filtrate. The precipitate was collected by a second filtration and washed with cold acetonitrile to yield a yellow powder. This solid (0.50 g, 1.0 mmol) will be dissolved in DMF and heated at 80° C. Iodomethane (0.62 mL, 10.0 mmol) will be added slowly and the reaction mixture will be heated for 12 h. Removal of the volatile components under reduced pressure will yield the product.

Workup

  1. temperatureat reflux for 30 min
  2. dissolutiondissolving the remaining solid
  3. stirringstirred
  4. temperatureat reflux for 30 min
  5. dissolutionpartially dissolving the solid
  6. temperatureto reflux for 3 h
  7. filtrationThe mixture was filtered hot
  8. customa precipitate quickly formed in the tan filtrate
  9. filtrationThe precipitate was collected by a second filtration
  10. washwashed with cold acetonitrile
  11. customto yield a yellow powder
  12. temperaturethe reaction mixture will be heated for 12 h
  13. customRemoval of the volatile components under reduced pressure
  14. customwill yield the product

Sources & evidence

ORD record
ord-e8f6f4d765e7432cb8ff762232e565cd
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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