Potassium Carbonate → HCID 86674183, compound

HRID 1038435Notes

Reaction equation

HRID 1038435 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1(C)C=CC(S([CH2:21][N+:22]#[C-:23])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[CH:9]=[C:8]([C:10]2[O:11][CH:23]=[N:22][CH:21]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 112173392-Fluoro-4-formylbenzonitrile

Product 1

HCID 86674183HCID 86674183, compoundYield 434.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100 mL round-bottom flask was added 2-fluoro-4-formylbenzonitrile 37 (1.00 g, 6.7 mmol), methanol (25 mL), p-toluene sulfonylmethyl isocyanide (1.44 g, 7.37 mmol), followed by potassium carbonate (1.195 g, 8.64 mmol). The reaction mixture was stirred at reflux for about 1.5 hour and followed by TLC. The solvent was then evaporated and saturated aq.NaHCO3 was added. The resultant suspension was extracted with CH2Cl2 (2×20 mL). Combined organic layers were washed with brine, dried (anhydrous Na2SO4), and concentrated to leave a yellow solid. Crude product was further purified by MPLC (Biotage) silica column chromatography (Acetone/hexane as an eluent) to afford 2-fluoro-4-(oxazol-5-yl)benzonitrile 38 (5.48 g, 79% yield). MS (ES) m/z 189 (M+H+).

Workup

  1. temperatureat reflux for about 1.5 hour
  2. customThe solvent was then evaporated
  3. additionNaHCO3 was added
  4. extractionThe resultant suspension was extracted with CH2Cl2 (2×20 mL)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried (anhydrous Na2SO4)
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. customCrude product was further purified by MPLC (Biotage) silica column chromatography (Acetone/hexane as an eluent)

Sources & evidence

ORD record
ord-df9804333e27450eb8745c5de8e43fbe
Source dataset
uspto-grants-2013_10
Patent number
US08551992B2

Reaction notes

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