Phosphorus oxychloride → HCID 22674092, compound

HRID 1173120Notes

Reaction equation

HRID 1173120 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

6-(4-Toluenesulfonylamino) isoquinoline (3.0 g, Production Example 21b) was dissolved in chloroform (100 ml). Under ice-cooling, m-chloroperbenzoic acid (2.57 g) was added thereto, 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 crystals were suspended in chloroform (83 ml) and phosphorous oxychloride (19 ml) was added thereto, followed by heating under reflux for 5 hours. After cooling, the solvent was evaporated. The residue was basified by adding an aqueous saturated sodium bicarbonate in an ice bath, and then the mixture was extracted with ethyl acetate. The extract was washed with brine and 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 crystals were recrystallized from ethanol, to give the title compound as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-7ee22318b0f94471ba67c7a764b9271f
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

Loading…