Dimethylformamide → HCID 18950416, compound

HRID 1492485Notes

Reaction equation

HRID 1492485 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+].C[N:17]([CH3:20])[CH:18]=O>>[CH3:6][C:3]1[C:4]2[N:5]=[CH:18][N:17]([C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[C:4]#[N:5])[C:20]=2[CH:8]=[CH:9][CH:2]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 18950416HCID 18950416, compound

Procedure

The title A compound (133 mg, 1.01 mmol), 2-fluorbenzonitrile (164 μL, 1.51 mmol) and finely ground potassium carbonate (279 mg, 2.02 mmol) were combined in 1 mL of N,N-dimethylformamide and heated to 80°. After stirring for 20 hours, the dimethylformamide was removed in vacuo and the brown solid residue was partitioned between saturated sodium bicarbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were dried over magnesium sulfate, filtered and the solvent removed. The residue was purified by flash chromatography (20 g silica gel, eluted with ethyl acetate, hexane) to provide 160 mg of the title B compound as a white solid.

Workup

  1. temperatureheated to 80°
  2. customthe dimethylformamide was removed in vacuo
  3. customthe brown solid residue was partitioned between saturated sodium bicarbonate and ethyl acetate
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed
  8. customThe residue was purified by flash chromatography (20 g silica gel, eluted with ethyl acetate, hexane)
  9. customto provide 160 mg of the title B compound as a white solid

Sources & evidence

ORD record
ord-71336cddb07e4abe95c90425c8ba1fe2
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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