Hydrochloric Acid → HCID 178509695, compound

HRID 431998Notes

Reaction equation

HRID 431998 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219426904-(3-cyanophenyl)-1-trityl-1H-imidazole

Product 1

HCID 178509695HCID 178509695, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3-cyanophenyl)-1-trityl-1H-imidazole (0.07 g, 0.17 mmol) in tetrahydrofuran (1.36 mL) was treated with 2N hydrochloric acid (0.68 mL) and the resulting mixture was heated at reflux for 45 minutes. After cooling the reaction mixture was concentrated in vacuo and the residue dissolved in dichloromethane (20 mL). The organic phase was successively washed with 1N sodium hydroxide (10 mL), water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography of the residues using 3% methanol in dichloromethane afforded 0.02 g (72%) of 4-(3-cyanophenyl)imidazole as a white solid.

Workup

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

Sources & evidence

ORD record
ord-5bf36b5f3bef435fa49030720762c082
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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