Potassium Hydroxide → HCID 70983740, compound

HRID 922613Notes

Reaction equation

HRID 922613 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. The crystals (0.66 g, 2.4 mmol) and 2-(bromomethyl)naphthalene (0.58 g, 2.6 mmol) were dissolved in 2 mL acetonitrile and refluxed for 3.5 h, during which time a white precipitate formed. The precipitate was collected via filtration of the reaction mixture and washed with acetonitrile to yield a white powder (1.02 g, 86% yield).). 1H NMR (300 MHz, DMSO-d6) 9.84 (1H, s, NCHN), 8.52 (1H, d, Ar), 7.8 (12H, m, Ar), 5.95 (2H, s, CH2), 5.83 (2H, 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-9b58e42a95b74a7ea00795bcc937c10b
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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