Potassium Hydroxide → HCID 70982700, compound

HRID 922616Notes

Reaction equation

HRID 922616 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>C(#N)C>[CH3:11][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[C:13]=1[N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]=[CH:4]1

Participants

5

Reactant 3

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

Product 1

HCID 70982700HCID 70982700, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

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 (0.4 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 (0.19 g, 40% yield). 1H NMR (300 MHz, DMSO-d6) 8.20 (3H, m, Ar), 8.10 (1H, s, NCHN), 8.01 (1H, d, Ar), 7.89-7.95 (2H, m, Ar), 7.74 (1H, dd, Ar), 5.51 (2H, s, CH2).

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

Sources & evidence

ORD record
ord-691f1dfd8ff243a08b1cec51137620ba
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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