Phosphorus oxychloride → HCID 18509400, compound

HRID 1356797Notes

Reaction equation

HRID 1356797 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:17](O)([CH:19]([CH3:21])[CH3:20])[CH3:18])[CH:14]=[CH:15][CH:16]=1)[CH3:9].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:1][C:2]([CH3:23])([CH3:24])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([CH:19]([CH3:20])[CH3:21])=[CH2:18])[CH:12]=1)[CH3:9]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18509422HCID 18509422, compound

Product 1

HCID 18509400HCID 18509400, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 20 (0.76 g; 2.32 mmol) was dissolved in pyridine (35 ml). While the solution was stirred at room temperature, phosphorus oxychloride (3.71 g; 24.2 mmol) was added dropwise. The mixture was heated for 3 hours at 100° C. while being stirred, and brought 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 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 0.41 g of the target compound (yield: 56.9%).

Workup

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

Sources & evidence

ORD record
ord-b95a55312e434c4c8b86317aa0c7a4b5
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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