4-[1-Hydroxycyclopent-1-yl-1-(imidazolyl)methyl]benzonitrile → 4-[1-Cyclopentylidene-1(imidazolyl)methyl]benzonitrile

HRID 846073Notes

Reaction equation

HRID 846073 reaction equation
O[C:2]1([CH:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1>S(Cl)(Cl)=O>[C:2]1(=[C:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 544681894-[1-Hydroxycyclopent-1-yl-1-(imidazolyl)methyl]benzonitrile

Product 1

HCID 542154114-[1-Cyclopentylidene-1(imidazolyl)methyl]benzonitrileYield 48.2%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

6.9 g of crude 4-[1-hydroxycyclopent-1-yl-1-(imidazolyl)methyl]benzonitrile is refluxed in 82 ml of thionyl chloride to 0.5 hour. Then the mixture is concentrated to dryness under vacuum, combined with 2N sodium hydroxide solution, extracted with dichloromethane, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, thus producing 3.1 g of 4-[1-cyclopentylidene-1(imidazolyl)methyl]benzonitrile as the free base, mp 108-110°.

Workup

  1. concentrationThen the mixture is concentrated to dryness under vacuum
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-626f2dc96c654f309b06116c687d21e0
Source dataset
uspto-grants-1992_08
Patent number
US05135937

Reaction notes

Loading…