Phosphorus oxychloride → HCID 9820138, compound

HRID 1356839Notes

Reaction equation

HRID 1356839 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:14]=[C:15]([C:20](O)([CH3:22])[CH3:21])[CH:16]=[C:17]([CH3:19])[CH:18]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]([CH3:22])=[CH2:21])[CH:14]=2)[CH3:11])=[CH:24][CH:25]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18509437HCID 18509437, compound

Product 1

HCID 9820138HCID 9820138, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 86 (0.40 g; 1.18 mmol) was dissolved in pyridine (20 ml). While the solution was stirred in an ice bath, phosphorus oxychloride (1.81 g; 11.8 mmol) was added dropwise. After completion of the addition, the mixture was removed from the ice bath, and stirred for 30 minutes at room temperature, followed by heating under reflux for 4 hours. The mixture was brought to room temperature, and poured into ice+saturated aqueous sodium bicarbonate solution. The mixture was neutralized with sodium bicarbonate, and extracted with chloroform (70 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1), to thereby yield 0.12 g of the target compound (yield: 31.6%).

Workup

  1. additionAfter completion of the addition
  2. customthe mixture was removed from the ice bath
  3. stirringstirred for 30 minutes at room temperature
  4. temperatureby heating
  5. temperatureunder reflux for 4 hours
  6. customwas brought to room temperature
  7. additionpoured into ice+saturated aqueous sodium bicarbonate solution
  8. extractionextracted with chloroform (70 ml)
  9. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  10. dry with materialwith saturated brine, and dried over sodium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-5f3cd118b9f0467692b29a234cb98027
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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