Potassium Carbonate → 2-Phenyl-4-(1-naphthyl)-5-methylimidazole

HRID 389229Notes

Reaction equation

HRID 389229 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:31])[C:19]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)=O>O1CCCC1>[C:3]1([C:2]2[NH:9][C:18]([CH3:31])=[C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80289Benzamidine, hydrochlorideHCID 2311612-Bromo-1'-propionaphthone2×

Product 1

HCID 589916112-Phenyl-4-(1-naphthyl)-5-methylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension consisting of 50.1 g (0.32 mol) of benzamidine hydrochloride, 133 g (0.96 mol) of potassium carbonate, and 250 mL of tetrahydrofuran was heated under reflux for one hour, and the foregoing toluene solution of 2-bromo-1′-propionaphthone was added dropwise over 50 minutes. After completion of addition, heated under reflux for 2 hours. Next, the reaction mixture was concentrated in vacuo, the resulting concentrate was diluted with 200 mL of toluene, and the solution was poured into 600 mL of water. The mixture was stirred to precipitate a solid. This solid was collected by filtration, successively washed with toluene and water, and then dried to obtain a crude crystal as a desired material. This crude crystal was recrystallized from DMF to obtain 48.1 g (yield: 52.9%) of a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. additionAfter completion of addition
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. concentrationNext, the reaction mixture was concentrated in vacuo
  7. concentrationthe resulting concentrate
  8. additionwas diluted with 200 mL of toluene
  9. additionthe solution was poured into 600 mL of water
  10. customto precipitate a solid
  11. filtrationThis solid was collected by filtration
  12. washsuccessively washed with toluene and water
  13. customdried

Sources & evidence

ORD record
ord-db98e58e9f0e439a8316faacd479ceaa
Source dataset
uspto-grants-2013_02
Patent number
US08378116B2

Reaction notes

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