Phosphorus oxychloride → HCID 18509405, compound

HRID 1356841Notes

Reaction equation

HRID 1356841 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:14]=[C:15]([C:19](O)([CH:21]([CH3:23])[CH3:22])[CH3:20])[CH:16]=[CH:17][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:26]=[CH:25][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH:21]([CH3:22])[CH3:23])=[CH2:20])[CH:14]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18509478HCID 18509478, compound

Product 1

HCID 18509405HCID 18509405, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 89 (0.30 g; 8.73×10−1 mmol) was dissolved in pyridine (20 ml). While the solution was stirred at room temperature, phosphorus oxychloride (1.34 g; 8.73 mmol) was added dropwise. After completion of the addition, the mixture was stirred for 6 hours at 100° C., and left to cool to room temperature. The mixture was poured into ice+saturated aqueous sodium bicarbonate solution, and extracted with chloroform (100 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=10:1), to thereby yield 0.19 g of the target compound as yellow oily matter (yield: 64.9%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred for 6 hours at 100° C.
  3. waitleft
  4. temperatureto cool to room temperature
  5. additionThe mixture was poured into ice+saturated aqueous sodium bicarbonate solution
  6. extractionextracted with chloroform (100 ml)
  7. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  8. dry with materialwith saturated brine, and dried over sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9144073fb18d4fc6adbff254923a7f78
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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