Phosphorus oxide (P4O10) → HCID 59536390, compound

HRID 445307Notes

Reaction equation

HRID 445307 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8][N:7]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 17683023HCID 17683023, compound

Product 1

HCID 59536390HCID 59536390, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 250-mL round-bottomed flask, 3,4-difluoro-N-phenethylbenzamide (1.97 g, 7.54 mmol) and phosphorus pentoxide (3.25 g, 22.9 mmol) were suspended into 40 mL of toluene. Phosphorus oxychloride (3.51 mL, 37.7 mmol) was added and the mixture was refluxed for overnight. The mixture was cooled to RT. The supernatant contained only the starting material and was removed. Ice water (75 mL) was added to the residue in the flask and stirred to break up the solid into powder. EtOAc was added and the pH was adjusted to ˜12 with 3N aqueous potassium hydroxide. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with water and saturated aqueous sodium chloride. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to afford a yellow viscous oil. The crude product was purified by silica gel chromatography (20-70% EtOAc in hexanes) to afford the title compound as a clear oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.17-7.52 (m, 7H) 3.78-3.92 (m, 2H) 2.73-2.89 (m, 2H)

Workup

  1. temperaturethe mixture was refluxed for overnight
  2. customwas removed
  3. additionIce water (75 mL) was added to the residue in the flask
  4. additionEtOAc was added
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with EtOAc
  7. washThe combined organic phases were washed with water and saturated aqueous sodium chloride
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto afford a yellow viscous oil
  12. customThe crude product was purified by silica gel chromatography (20-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7bc05aaa374042cb8228cc291e1fb766
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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