Acetonitrile → HCID 86719606, compound

HRID 922615Notes

Reaction equation

HRID 922615 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH-].[K+].C(#N)C.[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH2:29][N:30]1[C:34]([Cl:35])=[C:33]([Cl:36])[N:32]=[CH:31]1>O>[Cl-:2].[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][N+:32]1[C:33]([Cl:36])=[C:34]([Cl:35])[N:30]([CH2:29][C:20]2[CH:21]=[CH:22][C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:19]=2)[CH:31]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 70983740HCID 70983740, compound

Product 1

HCID 86719606HCID 86719606, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. filtrationwere collected by a second filtration
  2. temperaturerefluxed for 30 min
  3. temperaturethe mixture was refluxed overnight, during which time it
  4. extractionThe residue was extracted with dichloromethane (2×10 mL)
  5. dry with materialthe combined organic layers were dried with Mg2SO4
  6. customThe volatile components were removed under reduced pressure
  7. customyielding an oil
  8. extractionthe solution was extracted with toluene (2×)
  9. customThe combined aqueous layer was collected
  10. customto evaporate in air
  11. customA sticky brown solid was collected in low yield

Sources & evidence

ORD record
ord-a0af3afae1444198b7337e107018d448
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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