Phosphorus oxychloride → HCID 12069884, compound

HRID 1356795Notes

Reaction equation

HRID 1356795 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:18](O)([CH3:20])[CH3:19])[CH:14]=[C:15]([CH3:17])[CH:16]=1)[CH3:9].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([C:18]([CH3:20])=[CH2:19])[CH:12]=1)[CH3:9]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18509448HCID 18509448, compound

Product 1

HCID 12069884HCID 12069884, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 17 (1.08 g; 3.45 mmol) was dissolved in pyridine (50 ml). While the solution was stirred at room temperature, phosphorus oxychloride (5.28 g; 34.5 mmol) was added dropwise. The mixture was heated for 2.5 hours at 100° C. while being stirred, and left to cool to room temperature. The mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution (100 ml×2) and with saturated brine (×1), 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 0.53 g of the target compound (yield: 52.0%).

Workup

  1. temperatureThe mixture was heated for 2.5 hours at 100° C.
  2. stirringwhile being stirred
  3. waitleft
  4. temperatureto cool to room temperature
  5. additionThe mixture was poured into ice+saturated aqueous sodium bicarbonate solution
  6. extractionfollowed by extraction with chloroform (100 ml)
  7. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (100 ml×2) and with saturated brine (×1)
  8. dry with materialdried 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-9d53404c5c0a408caed86eb0e09576a4
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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