Hydrochloric Acid → HCID 178420123, compound

HRID 2216892

Reaction equation

HRID 2216892 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[CH:9][N:10](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:11]=1.Cl>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[CH:9][NH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219426882-(1-trityl-1H-imidazol-4-yl)pyridine

Product 1

HCID 178420123HCID 178420123, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the crude 4-(2-pyridyl)-1-trityl-1H-imidazole (0.69 g) in tetrahydrofuran (14 mL) was treated with 2 N hydrochloric acid (7.2 mL) and heated at reflux for 45 minutes. After cooling the reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane (20 mL). The organic solution was successively washed with aqueous 1N sodium hydroxide (10 mL), water (20 mL) and brine (20 mL). The organic solution was then dried over anhydrous sodium sulfate, filtered, and concentrated in-vacuo to afford 0.12 g of crude 4-(2-pyridyl)imidazole, as a sticky white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 minutes
  3. temperatureAfter cooling the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane (20 mL)
  6. washThe organic solution was successively washed with aqueous 1N sodium hydroxide (10 mL), water (20 mL) and brine (20 mL)
  7. dry with materialThe organic solution was then dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-8053cc3a78204a2fb63d875d8fbc1164
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Linked notes

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