Phenol → HCID 22136223, compound

HRID 1826836Notes

Reaction equation

HRID 1826836 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH2:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14]>CS(C)=O>[O:7]([C:15]1[CH:16]=[CH:17][CH:18]=[C:11]([NH2:10])[C:12]=1[C:13]#[N:14])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 5226592-Amino-6-fluorobenzonitrile

Product 1

HCID 22136223HCID 22136223, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

Phenol (2.06 g, 22 mmol) was dissolved in dry dimethyl sulfoxide (25 mL), and sodium hydride (0.53 g, 22 mmol) was added in portions, and the mixture stirred for 1 hour under argon. 2-Amino-6-fluorobenzonitrile (2.72 g, 20 mmol) was added and the mixture heated to 110° C. overnight. The solvent was evaporated in vacuo, and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water (5×), brine (1×) dried over anhydrous Na2SO4 filtered, and evaporated to give the crude product which was then chromatographed on silica gel eluted with 0–20% ethyl acetate in hexane to give the title compound as a white amorphous solid. Recrystallization from carbon tetrachloride, hexane gave a white crystalline solid. mp 66–67° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water (5×), brine (1×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product which
  8. customwas then chromatographed on silica gel
  9. washeluted with 0–20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0290b42b136d42b2b49264f75f3d1375
Source dataset
uspto-grants-2006_05
Patent number
US07053099B1

Reaction notes

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