Phosphorus oxychloride → HCID 59574224, compound

HRID 2092040Notes

Reaction equation

HRID 2092040 reaction equation
O=[C:2]1[C:7]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[CH:6][CH:5]=[N:4][NH:3]1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 595748041H-Isoindole-1,3(2H)-dione, 2-[(2,3-dihydro-3-oxo-4-pyridazinyl)methyl]-

Product 1

HCID 59574224HCID 59574224, compoundYield 89%

Procedure

2-[(3-Oxo-2,3-dihydropyridazin-4-yl)methyl]-1H-isoindole-1,3(2H)-dione (1.1 g, 4.27 mmol) was mixed with phosphoryl chloride (10 mL) and heated to reflux for 1 hour. After completion of the reaction, phosphoryl chloride was removed under reduced pressure. The resulting residue was diluted with chloroform and water. The organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum distillation. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give the desired product (89% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. customwas removed under reduced pressure
  4. additionThe resulting residue was diluted with chloroform and water
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by vacuum distillation
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-cab618e620a041d9b7dba1373d9ae338
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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