Aniline → HCID 23509657, compound

HRID 1882772Notes

Reaction equation

HRID 1882772 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]=1[C:13]#[N:14]>CS(C)=O>[C:2]1([NH:1][C:11]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:12]=2[C:13]#[N:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 24758Sodium hydrideHCID 235096522-Cyano-3-fluorobiphenyl

Product 1

HCID 23509657HCID 23509657, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Aniline (0.168 g, 1.8 mmol) was dissolved in dimethyl sulfoxide (3 mL) and stirred under argon at room temperature. Sodium hydride (0.0043 g, 1.8 mmol) was added and a deep purple color developed while the mixture was stirred at room temperature for 1 hour. The mixture was cooled to 0° C. in an ice bath and the product of example 12a above, 2-fluoro-6-phenylbenzonitrile, (0.295 g, 1.5 mmol) dissolved in dimethyl sulfoxide (2 mL) was added and the mixture stirred at room temperature 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 0-30% CH2Cl2 in hexane to give the title compound as a white amorphous solid. ES (+) MS m/e=271 (MH+)

Workup

  1. stirringwas stirred at room temperature for 1 hour
  2. temperatureThe mixture was cooled to 0° C. in an ice bath
  3. additionwas added
  4. stirringthe mixture stirred at room temperature overnight
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was partitioned between ethyl acetate and water
  7. washThe organic phase was washed with water (5×), brine (1×)
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customto give the crude product which
  12. customwas then chromatographed on silica gel
  13. washeluted with 0-30% CH2Cl2 in hexane

Sources & evidence

ORD record
ord-96840d836ee046a4b100dd1951904438
Source dataset
uspto-grants-2004_07
Patent number
US06759410B1

Reaction notes

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