Triethylamine → HCID 18437857, compound

HRID 457368Notes

Reaction equation

HRID 457368 reaction equation
[CH2:1]([N:3](CC)CC)C.CS(Cl)(=O)=O.[CH2:13]([N:17]1[C:21]([CH2:22]O)=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:19]=[C:18]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:14][CH2:15][CH3:16]>C(#N)C.[C-]#N.C([N+](CC)(CC)CC)C>[CH2:13]([N:17]1[C:21]([CH2:22][C:1]#[N:3])=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:19]=[C:18]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18437780HCID 18437780, compound

Product 1

HCID 18437857HCID 18437857, compound

Reagents, catalysts & solvents 2

HCID 3014735Tetraethylammonium cyanideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Triethylamine (1.0 ml, 7.18 mmol) and methanesulfonyl chloride (0.37 ml, 4.89 mmol) are added to a stirred solution of (3-butyl-2,5-diphenyl-3H-imidazol-4-yl)-methanol (1.0 g, 3.26 mmol)(185) in anhydrous acetonitrile (30 mL) at 0° C. After proceeding for 1 hour the reaction is concentrated at 60° C. to remove all solvent and excess MsCl. Cold acetonitrile is added to precipitate triethylammonium chloride, which is then removed by filtration. The remaining solution of mesylate product is reduced to a 30 ml volume; tetraethylammonium cyanide (1.53 g, 9.79 mmol) is added to the solution, and the reaction is heated at 60° C. overnight. Solvent is removed in vacuo and the crude product dissolved in ethyl acetate (100 mL). The organic layer is washed with saturated sodium bicarbonate (2×100 mL), brine (1×100 mL) and dried over magnesium sulfate. The sample is filtered, concentrated and purified by flash chromatography on SiO2 using an eluent of 2:3 acetate:hexane to afford (3-butyl-2,5-diphenyl-3H-imidazol-4-yl)-acetonitrile (187) as a light orange oil.

Workup

  1. concentrationthe reaction is concentrated at 60° C.
  2. customto remove all solvent and excess MsCl
  3. additionCold acetonitrile is added
  4. customto precipitate triethylammonium chloride, which
  5. customis then removed by filtration
  6. customSolvent is removed in vacuo
  7. dissolutionthe crude product dissolved in ethyl acetate (100 mL)
  8. washThe organic layer is washed with saturated sodium bicarbonate (2×100 mL), brine (1×100 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationThe sample is filtered
  11. concentrationconcentrated
  12. custompurified by flash chromatography on SiO2 using an eluent of 2:3 acetate

Sources & evidence

ORD record
ord-c1ae0cc2db134d508db2e8374b640960
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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