Dimethylformamide → HCID 18950378, compound

HRID 1492483Notes

Reaction equation

HRID 1492483 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH3:16][N:17]([CH3:20])C=O>O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[N:17]1[C:20]2[C:6](=[C:3]([CH3:4])[CH:2]=[CH:9][CH:8]=2)[CH:7]=[CH:16]1)#[N:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 18950378HCID 18950378, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

The title B compound of Example 4 (1.042 g, 7.94 mmol, 1.0 eq.) was combined with 2-fluorobenzonitrile (1.29 ml, 11.91 mmol, 1.5 eq.) and potassium carbonate (2.195 g, 15.88 mmol, 2.0 eq.) in dimethylformamide (7.94 ml, 1M) and heated at 150° C. for 4 hours. The reaction was then cooled to room temperature, diluted with water (20 ml), and extracted three times with ethyl acetate. The organic extracts were washed with water and aqueous saturated sodium chloride, dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on Merck silica gel (50 g) eluting with chloroform:hexane (1:3) followed by (1:1) to give the title A compound (1.57 g).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with ethyl acetate
  3. washThe organic extracts were washed with water and aqueous saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered through magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on Merck silica gel (50 g)
  8. washeluting with chloroform:hexane (1:3)

Sources & evidence

ORD record
ord-2f6f8288adf34f8f854fd0bbb132ef4f
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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