Phosphorus oxychloride → HCID 18327906, compound

HRID 1250303Notes

Reaction equation

HRID 1250303 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]=[CH:12][C:11](O)([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[N:15]=[CH:16][CH:17]=[CH:18][N:19]=2)=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18328032HCID 18328032, compound

Product 1

HCID 18327906HCID 18327906, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.11 g of the compound of step 1 of Example 25 was dissolved in 30 ml of pyridine, then 1.0 ml (1.4 equivalents) of phosphorus oxychloride was added under ice cooling and the result was agitated for 15 hours. The pyridine was distilled off under reduced pressure, an aqueous solution of 10% sodium hydroxide was added and extraction was performed by methylene chloride. The organic layer was washed with saturated saline and was dried by anhydrous magnesium sulfate, then the solvent was distilled off and the resultant crude product was refined with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the above-referenced compound in an amount of 1.01 g (yield of 51%).

Workup

  1. distillationThe pyridine was distilled off under reduced pressure
  2. additionan aqueous solution of 10% sodium hydroxide was added
  3. extractionextraction
  4. washThe organic layer was washed with saturated saline
  5. dry with materialwas dried by anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customto obtain the above-referenced compound in an amount of 1.01 g (yield of 51%)

Sources & evidence

ORD record
ord-b6c8df10395e43e1be627324484d5cb5
Source dataset
uspto-grants-2002_01
Patent number
US06337397B1

Reaction notes

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