Potassium Hydroxide → HCID 70983740, compound

HRID 922614Notes

Reaction equation

HRID 922614 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].Cl.Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>C(#N)C>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 1400184,5-DichloroimidazoleHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 70983740HCID 70983740, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4,5-Dichloroimidazole (2.00 g, 14.6 mmol) was dissolved in 15 mL acetonitrile in a round bottom flask. Potassium hydroxide (0.90 g, 16.0 mmol) was added and the mixture was refluxed for 15 min. Concurrently, 2-chloromethylquinoline hydrochloride (3.13 g, 14.6 mmol) and potassium hydroxide (0.82 g, 14.6 mmol) were added to a second round bottom flask and stirred in 60 mL acetonitrile at reflux for 10 min. The contents of the second flask were added to the first, and the combined mixture was refluxed overnight, during which time a white precipitate formed. The reaction mixture was filtered hot, yielding a clear, tan filtrate. Slow evaporation and cooling of the filtrate yielded tan crystals of 1-(quinolin-2-ylmethyl)-4,5-dichloroimidazole, which were collected by a second filtration. 2-Chloromethylquinoline hydrochloride (0.19 g, 0.88 mmol) and potassium hydroxide (0.05 g, 0.90 mmol) were added to 5 mL acetonitrile and refluxed for 30 min. Crystals of 1-(quinolin-2-ylmethyl)-4,5-dichloroimidazole (0.1087 g, 0.39 mmol) were added, and the mixture was refluxed overnight, during which time it became red in color and viscous. The residue was extracted with dichloromethane (2×10 mL) and the combined organic layers were dried with Mg2SO4. The volatile components were removed under reduced pressure yielding an oil. The oil was dissolved in water, and the solution was extracted with toluene (2×). The combined aqueous layer was collected and the solvent allowed to evaporate in air. A sticky brown solid was collected in low yield. 1H NMR (300 MHz, DMSO-d6) 10.03 (1H, s, NCHN), 8.55 (2H, d, Ar), 8.07 (2H, d, Ar), 7.89 (2H, d, Ar), 7.79 (2H, t, Ar), 7.74 (2H, d, Ar), 7.67 (2H, t, Ar), 6.07 (4H, s, CH2).

Workup

  1. temperaturethe mixture was refluxed for 15 min
  2. temperatureat reflux for 10 min
  3. additionThe contents of the second flask were added to the first, and the combined mixture
  4. temperaturewas refluxed overnight, during which time a white precipitate
  5. customformed
  6. filtrationThe reaction mixture was filtered hot
  7. customyielding a clear, tan filtrate
  8. customevaporation
  9. temperaturecooling of the filtrate

Sources & evidence

ORD record
ord-088499303428450a88ccc4950dbfd6b6
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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