Phosphorus oxychloride → HCID 22674092, compound

HRID 1005678Notes

Reaction equation

HRID 1005678 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[N:16][CH:15]=[CH:14]3)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:22]C1C=CC=C(C(OO)=O)C=1.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[Cl:22][C:17]1[C:18]2[C:13](=[CH:12][C:11]([NH:10][S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:21])=[CH:6][CH:5]=3)(=[O:8])=[O:9])=[CH:20][CH:19]=2)[CH:14]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 70297m-Chloroperbenzoic acidHCID 22674130HCID 22674130, compound

Product 1

HCID 22674092HCID 22674092, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In chloroform (100 ml) was dissolved 3.0 g of 6-(4-toluenesulfonylamino)isoquinoline (Preparation Example 21), and m-chloroperbenzoic acid (2.57 g) was added thereto under ice-cooling, followed by stirring at room temperature overnight. The solvent was evaporated, and the resulting crystals were washed with diethyl ether, collected by filtration and dried, to give pale yellow crystals. The obtained crystals were suspended in chloroform (83 ml), and phosphorus oxychloride (19 ml) was added thereto, followed by heating under reflux for 5 hours. After cooling, the solvent was evaporated, and the residue was basified with an aquesou sodium bicarbonate in an ice-bath, followed by extracting with ethyl acetate, The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified by silica gel column, to give crude crystals of the title compound (1.630 g, 49.40%). The crude crysatals were recrystallized from ethanol, to give the title compound as colorless crystals.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. customThe solvent was evaporated
  4. washthe resulting crystals were washed with diethyl ether
  5. filtrationcollected by filtration
  6. customdried
  7. customto give pale yellow crystals
  8. temperatureby heating
  9. temperatureunder reflux for 5 hours
  10. temperatureAfter cooling
  11. customthe solvent was evaporated
  12. customthe residue was basified with an aquesou sodium bicarbonate in an ice-bath
  13. extractionby extracting with ethyl acetate
  14. washThe extract was washed with brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. customthe solvent was evaporated
  17. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-7a63818d78584ea8903c0fe8b35f5602
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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