HCID 54515600, compound → HCID 178442820, compound

HRID 1756954Notes

Reaction equation

HRID 1756954 reaction equation
[C:1]([C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H]>C(O)(=O)C.[Pd]>[CH2:1]([C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 54515600HCID 54515600, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178442820HCID 178442820, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Twenty percent Pd/C (1 g) was added to a solution of 4-(1-dodecynyl)-1-(triphenylmethyl) imidazole (2.39 g, 5 mmol) in glacial acetic acid (100 mL), along with 50 psi of hydrogen gas. Stirred for 16 hours and concentrated in vacuo. The residue was made basic with saturated Na2CO3, neutralized with 1N HCl, and extracted with ether. The ether layer was dried over MgSO4, filtered, and concentrated to give an oily white solid. Recrystallized from hexanes to give the title compound as a white solid (1.06 g, 90%); mp 69°-71° C.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ether
  3. dry with materialThe ether layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oily white solid
  7. customRecrystallized from hexanes

Sources & evidence

ORD record
ord-96cf08a3e714400fb9a07f9234b2da3f
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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